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• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
  • C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
  • C07F7/02—Silicon compounds
  • C07F7/08—Compounds having one or more C—Si linkages
  • C07F7/0834—Compounds having one or more O-Si linkage
  • C07F7/0838—Compounds with one or more Si-O-Si sequences
  • C07F7/0872—Preparation and treatment thereof
  • C07F7/089—Treatments not covered by a preceding group
• • C—CHEMISTRY; METALLURGY
  • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
  • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
  • C08G77/00—Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule
  • C08G77/04—Polysiloxanes
  • C08G77/06—Preparatory processes
• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
  • C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
  • C07F7/02—Silicon compounds
  • C07F7/08—Compounds having one or more C—Si linkages
• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
  • C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
  • C07F7/02—Silicon compounds
  • C07F7/08—Compounds having one or more C—Si linkages
  • C07F7/0834—Compounds having one or more O-Si linkage
  • C07F7/0838—Compounds with one or more Si-O-Si sequences
• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
  • C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
  • C07F7/02—Silicon compounds
  • C07F7/08—Compounds having one or more C—Si linkages
  • C07F7/0834—Compounds having one or more O-Si linkage
  • C07F7/0838—Compounds with one or more Si-O-Si sequences
  • C07F7/0872—Preparation and treatment thereof
  • C07F7/0874—Reactions involving a bond of the Si-O-Si linkage
• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
  • C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
  • C07F7/02—Silicon compounds
  • C07F7/08—Compounds having one or more C—Si linkages
  • C07F7/12—Organo silicon halides
• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
  • C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
  • C07F7/02—Silicon compounds
  • C07F7/08—Compounds having one or more C—Si linkages
  • C07F7/18—Compounds having one or more C—Si linkages as well as one or more C—O—Si linkages
• • C—CHEMISTRY; METALLURGY
  • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
  • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
  • C08G77/00—Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule
  • C08G77/04—Polysiloxanes
  • C08G77/38—Polysiloxanes modified by chemical after-treatment
  • C08G77/382—Polysiloxanes modified by chemical after-treatment containing atoms other than carbon, hydrogen, oxygen or silicon
  • C08G77/385—Polysiloxanes modified by chemical after-treatment containing atoms other than carbon, hydrogen, oxygen or silicon containing halogens

Definitions

• the present invention relates to a method for producing a compound and the compound.
• Patent Document 1 discloses compounds containing perfluoroalkyl groups or fluoroalkyl groups that can be used as alignment agents.
• the inventors focused on compounds having a siloxane structure, which is a compound containing a Si atom, as such compounds, and produced compounds having a siloxane structure by hydrosilylation. However, they found that the above method had problems such as a large amount of by-products and an insufficient yield of the desired compound.
• a method for producing a compound comprising a step 3 of reacting the compound represented by the above formula (4) produced by the method for producing a compound according to [1] with a compound represented by formula (5) described below to obtain a compound represented by formula (6) described below.
• [4] The method for producing the compound according to any one of [1] to [3], wherein R, R 1 and R 2 are methyl groups.
• [5] A compound represented by formula (7) described below.
• [6] The compound according to [5], wherein L is an n-propylene group.
• [7] The compound according to [5] or [6], wherein R, R 1 and R 2 are methyl groups.
• the present invention there is provided a method for producing a compound, which can easily produce an intermediate useful in producing a compound having a siloxane structure. Furthermore, the present invention can provide a compound that is useful in producing a compound having a siloxane structure.
• a numerical range expressed using “to” means a range that includes the numerical values before and after “to” as the lower and upper limits.
• the “content” of the component means the total content of those two or more components.
• the upper limit or lower limit described in a certain numerical range may be replaced with the upper limit or lower limit of another numerical range described stepwise.
• the upper limit or lower limit described in a certain numerical range may be replaced with a value shown in the examples.
• a combination of two or more preferred aspects is a more preferred aspect.
• a formula showing a chemical structure contains a plurality of identical symbols showing the type or number of groups, unless otherwise specified, the contents of the plurality of identical symbols are independent of each other, and the contents of the plurality of identical symbols may be the same or different.
• a formula showing a chemical structure contains a plurality of groups of the same type (for example, alkyl groups, etc.)
• the specific contents of the plurality of groups of the same type are independent of each other, unless otherwise specified, and the specific contents of the groups of the same type may be the same or different.
• the bonding direction of divalent groups described in this specification is not limited unless otherwise specified.
• Y when Y is -COO- in a compound represented by the formula "X-Y-Z", Y may be -CO-O- or -O-CO-.
• the above compound may be "X-CO-O-Z" or "X-O-CO-Z”.
• the resulting crude product may be purified, if necessary, by one or more operations selected from washing, extraction, drying, filtration, concentration, recrystallization, reprecipitation, crystallization, centrifugation, adsorption, column purification, and sublimation purification.
• the process for producing the compound of the present invention includes step 1 of reacting a compound represented by formula (1) described below (also referred to as “compound (1)”) with a compound represented by formula (2) described below (also referred to as “compound (2)”) to obtain a compound represented by formula (3) described below (also referred to as “compound (3)”), and step 2 of obtaining a compound represented by formula (4) described below (also referred to as "compound (4)") from compound (3).
• the method for producing a compound of the present invention includes step 1 of reacting a compound (1) having a siloxane structure with a compound (2) to synthesize a compound (3). This makes it possible to easily form a desired siloxane structure that may have a branched structure.
• the compound (4) obtained by converting the compound (3) in step 2 has a leaving group represented by X linked to the siloxane structure obtained in step 1 by an alkylene group. Therefore, the compound (4) can react simply and efficiently with a functional group having nucleophilicity (e.g., a carboxy group and a hydroxy group).
• a functional group having nucleophilicity e.g., a carboxy group and a hydroxy group.
• the method for producing a compound of the present invention makes it possible to produce an intermediate compound that can simply synthesize a compound having a desired siloxane structure.
• Step 1 is a step of reacting compound (1) with compound (2) to obtain compound (3).
• compound (2) is a compound that has been modified by reacting compound (1) with compound (2) to obtain compound (3).
• each R independently represents an alkyl group.
• the alkyl group may be linear, branched, or cyclic, and is preferably linear.
• the alkyl group preferably has 1 to 10 carbon atoms, more preferably 1 to 6 carbon atoms, even more preferably 1 to 3 carbon atoms, and most preferably 1 carbon atom.
• a plurality of R's may be the same or different.
• R is preferably a linear alkyl group having 1 to 6 carbon atoms, more preferably a linear alkyl group having 1 to 3 carbon atoms, and further preferably a methyl group.
• R 1 and R 2 each independently represent an alkyl group or -(O-SiR 3 R 4 ) l -O-Si(R 5 ) 3 .
• the preferred embodiments of the alkyl group represented by R1 and R2 are the same as the alkyl group represented by R described above.
• each l independently represents an integer of 0 or more. As l, an integer of 0 to 20 is preferable, an integer of 0 to 10 is more preferable, and an integer of 0 to 6 is even more preferable.
• R 3 to R 5 each independently represent an alkyl group.
• the preferred embodiments of the alkyl group represented by R 3 to R 5 are the same as the alkyl group represented by R described above.
• R 1 and R 2 are preferably a linear alkyl group having 1 to 3 carbon atoms, or a substituent SI in which R 3 to R 5 are linear alkyl groups having 1 to 3 carbon atoms, more preferably a linear alkyl group having 1 to 3 carbon atoms, and further preferably a methyl group.
• m represents an integer of 0 or more.
• an integer of 0 to 20 is preferable, an integer of 0 to 15 is more preferable, and an integer of 0 to 10 is even more preferable.
• each R independently represents an alkyl group.
• the definition and preferred embodiments of R in formula (2) are the same as those of R in formula (1).
• L represents an alkylene group.
• the alkylene group may be linear, branched, or cyclic, but is preferably linear in terms of the reaction efficiency in step 1 and the availability of raw materials.
• the alkylene group preferably has 1 to 10 carbon atoms, more preferably 1 to 6 carbon atoms, further preferably 2 to 4 carbon atoms, and particularly preferably 3 carbon atoms.
• the alkylene group is preferably a linear alkylene group having 1 to 6 carbon atoms, more preferably a linear alkylene group having 2 to 4 carbon atoms, and even more preferably an n-propylene group.
• n an integer between 1 and 3.
• R, R 1 , R 2 , and m in formula (3) are the same as R, R 1 , R 2 , and m in formula (1), respectively, and n and L in formula (3) are the same as n and L in formula (2), respectively.
• step 1 The specific procedure of step 1 is not particularly limited as long as compound (3) can be obtained from compound (1) and compound (2).
• reaction conditions for a conventionally known nucleophilic substitution reaction can be appropriately adopted.
• the reaction in step 1 is preferably carried out in a solvent.
• the solvent is not particularly limited, and examples thereof include aromatic hydrocarbon solvents such as toluene and xylene; aliphatic hydrocarbon solvents such as pentane, hexane, heptane, octane, and cyclohexane; ketone solvents such as acetone, methyl ethyl ketone, and cyclopentanone; ether solvents such as ethylene glycol dimethyl ether, tetrahydrofuran, diethyl ether, and dioxane; ester solvents such as ethyl acetate and butyl acetate; aprotic polar solvents such as acetonitrile, N,N-dimethylformamide, N,N-dimethylacetamide, and N-methylpyrrolidone; and chlorinated hydrocarbon solvents such as chloroform and dichloromethane.
• the above solvents may
• the reaction in step 1 is preferably carried out in the presence of a base.
• the base include organic bases and inorganic bases.
• the organic base include nitrogen-containing aromatic heterocyclic compounds such as pyridine and pyrimidine, nitrogen-containing aliphatic compounds such as triethylamine, trimethylamine, N,N-diisopropylethylamine, and 1,8-diazabicyclo[5.4.0]-7-undecene (DBU), and metal alkoxides such as potassium tert-butoxide.
• the inorganic base include sodium carbonate, sodium bicarbonate, potassium carbonate, cesium carbonate, sodium hydroxide, potassium hydroxide, cesium hydroxide, sodium phosphate, potassium phosphate, and sodium acetate.
• the amounts of compound (1) and compound (2) used are not particularly limited, but the amount of compound (1) used per mole of compound (2) is preferably 1n to 2n moles, more preferably 1n to 1.5n moles, and even more preferably 1n to 1.2n moles.
• the reaction temperature can be appropriately adjusted depending on the compound and solvent used, and is preferably from -20 to 50°C, more preferably from 0 to 30°C.
• the reaction time can be appropriately adjusted depending on the compound and solvent used, and is preferably 0.5 to 10 hours, more preferably 1 to 5 hours.
• Step 2 is a step of obtaining compound (4) from compound (3).
• Compound (4) and specific steps will be described below in the stated order.
• R, R 1 , R 2 , m, n, and L in formula (4) are the same as R, R 1 , R 2 , m, n, and L in formula (3), respectively.
• X represents a bromine atom or an iodine atom.
• X is preferably an iodine atom in that the reactivity of the compound represented by formula (4) is superior.
• Examples of compound (4) include compounds represented by the following formulas (4-1) to (4-3).
• R, R 1 , R 2 , m, L and X in formulas (4-1) to (4-3) are the same as R, R 1 , R 2 , m, L and X in formula (4), respectively.
• the group represented by X in compound (4) can function as a leaving group, and is therefore useful as an intermediate that can easily introduce a siloxane structure into a compound that contains a functional group having nucleophilicity (e.g., a carboxy group and a hydroxy group).
• the compound represented by formula (4) may be used for purposes other than as an intermediate.
• Examples of compound (4) are shown below, but the present invention is not limited thereto.
• Et represents an ethyl group
• iPr represents an isopropyl group.
• step 2 The specific procedure of step 2 is not particularly limited as long as compound (4) can be obtained from compound (3).
• conditions for a conventionally known conversion reaction of a leaving group can be appropriately adopted.
• the compound (4) may be reacted with an iodide or bromide.
• Examples of the iodides include metal iodides such as sodium iodide, potassium iodide, calcium iodide, and magnesium iodide.
• Examples of the bromides include metal bromides such as sodium bromide, potassium bromide, calcium bromide, and magnesium bromide.
• the amount of the iodide or bromide used is not particularly limited, but is preferably 1 to 20 moles, more preferably 1.5 to 15 moles, per mole of compound (3).
• the above reaction is preferably carried out in a solvent.
• the above-mentioned solvents for example, the solvents used in step 1 above, can be used.
• the reaction temperature can be appropriately adjusted depending on the compound and solvent used, and is preferably 30 to 150°C, more preferably 60 to 100°C.
• the reaction time can be appropriately adjusted depending on the compound and solvent used, and is preferably 1 to 48 hours, more preferably 3 to 30 hours.
• the compound production method of the present invention is preferably used for producing a compound having a siloxane structure.
• the compound (4) produced by the compound production method of the present invention is preferably used for producing a compound having a siloxane structure.
• a compound having a siloxane structure can be produced by a nucleophilic substitution reaction between compound (4) and a compound containing a nucleophilic functional group such as a hydroxy group or a carboxy group.
• An example of the application of the method for producing a compound of the present invention is a method for producing a compound having a siloxane structure and an aromatic ring by Step 3 shown below.
• Step 3 is a step of reacting compound (4) with a compound represented by formula (5) (also referred to as “compound (5)”) to obtain a compound represented by formula (6) (also referred to as “compound (6)").
• a compound represented by formula (5) also referred to as “compound (5)”
• a compound represented by formula (6) also referred to as “compound (6)”
• Ar represents an aromatic ring.
• the aromatic ring may be either a monocyclic ring or a polycyclic ring.
• the aromatic ring may be either an aromatic hydrocarbon ring or an aromatic heterocycle.
• the aromatic ring preferably has 5 to 20 member atoms, more preferably 5 to 12 member atoms, and even more preferably 6 to 10 member atoms.
• aromatic hydrocarbon rings such as a benzene ring, a naphthalene ring, an anthracene ring, a pyrene ring, a phenanthrene ring, and a fluorene ring, as well as a pyridine ring, a pyrimidine ring, a pyridazine ring, a pyrazine ring, a triazine ring, a tetrazine ring, a quinoxaline ring, a pyrrole ring, a furan ring, a thiophene ring, an imidazole ring, an oxazole ring, a thiazole ring, a benzopyrrole ring, a benzofuran ring, a benzothiophene ring, a benzimidazole ring, a benzoxazole ring, a benzothiazole ring, a benzothiazo
• aromatic heterocycles include a furan ring, a naphthothiophene ring, a naphthoimidazole ring, a naphthoxazole ring, a pyrroloimidazole ring, an imidazoxazole ring, a thienothiazole ring, a benzothiadiazole ring, a benzodithiophene ring, a thienothiophene ring, a thiazolothiazole ring, a naphthodithiophene ring, and a benzothienobenzothiophene ring.
• a benzene ring, a naphthalene ring, an anthracene ring, a pyridine ring, a pyrimidine ring, a pyrrole ring, a furan ring, or a thiophene ring is preferable, and a benzene ring is more preferable.
• each Y independently represents a hydroxy group or a carboxy group.
• the plurality of Y's are preferably the same group. That is, in formula (5), it is preferable that all of the p Y's present represent a hydroxy group or all of the p Y's represent a carboxy group.
• p represents an integer of 1 or more. p is preferably 1 to 6, more preferably 1 to 3, and further preferably 1 or 2.
• each A independently represents a substituent other than a carboxy group, provided that when A represents a hydroxy group, Y represents a carboxy group.
• substituent other than the carboxy group represented by A include a halogen atom, an alkyl group, an alkenyl group, an alkynyl group, an aryl group, a heterocyclic group, a hydroxy group, an alkoxy group, an amino group, an aryloxy group, a formyl group, an acyl group, an alkoxycarbonyl group, an aryloxycarbonyl group, an acyloxy group, an acylamino group, an aminocarbonylamino group, an alkoxycarbonylamino group, an aryloxycarbonylamino group, an alkylsulfonylamino group, an arylsulfonylamino group, an alkylthio ...
• substituents examples include an arylthio group, an alkylsulfinyl group, an arylsulfinyl group, an alkylsulfonyl group, an arylsulfonyl group, a silyloxy group, a heterocyclic oxy group, a carbamoyl group, a carbamoyloxy group, a heterocyclic thio group, a sulfamoyl group, an arylazo group, a heterocyclic azo group, an imido group, a phosphino group, a phosphinyl group, a phosphinyloxy group, a phosphinylamino group, a hydrazino group, an imino group, a cyano group, a nitro group, a mercapto group, a sulfo group, a hydroxamic acid group, a sulfino group, a boronic acid group
• substituents may further have the substituents exemplified above as the substituents.
• the substituent is preferably a hydroxy group, a formyl group, an acyl group, an alkyl group, or a halogen atom.
• q represents an integer of 0 or more. q is preferably an integer of 0 to 6, and more preferably an integer of 0 to 3.
• R, R 1 , R 2 , m, n, and L in formula (6) are the same as R, R 1 , R 2 , m, n, and L in formula (4), and p, Ar, A, and q in formula (6) are the same as p, Ar, A, and q in formula (5).
• Z represents —O— or —OCO—.
• Z when Y is a hydroxy group, Z is --O--, and when Y is a carboxy group, Z is --OCO--.
• the use of the compound represented by formula (6) is not particularly limited, and it may be used, for example, as a surfactant and a surface modifier, or as an intermediate.
• Examples of compound (6) are shown below, but the present invention is not limited thereto.
• Et represents an ethyl group
• iPr represents an isopropyl group.
• step 3 The specific procedure of step 3 is not particularly limited as long as compound (6) can be obtained from compound (4) and compound (5).
• reaction conditions for a conventionally known nucleophilic substitution reaction can be appropriately adopted.
• the reaction in the above step 3 is preferably carried out in a solvent.
• the solvent include the solvents that can be used in step 1 described above.
• the reaction in step 3 is preferably carried out in the presence of a base.
• the base include the bases that can be used in step 1 described above.
• the amounts of compound (5) and compound (4) used are not particularly limited, but the amount of compound (4) used is preferably 1p to 2p moles, more preferably 1p to 1.5p moles, and even more preferably 1p to 1.2p moles, per mole of compound (5).
• p is p in formula (5).
• the amount of compound (4) used is preferably 2 to 4 moles, more preferably 2 to 3 moles, and even more preferably 2 to 2.4 moles, per mole of compound (5).
• the reaction temperature can be appropriately adjusted depending on the compound and solvent used, and is preferably 20 to 150° C., more preferably 40 to 100° C., and even more preferably 50 to 80° C.
• the reaction time can be appropriately adjusted depending on the compound and solvent used, and is preferably 1 to 48 hours, and more preferably 5 to 24 hours.
• step 3 The reaction in which compound (4) produced by the method for producing a compound of the present invention is used as an intermediate is not limited to step 3, and compound (4) may be used in a reaction with a compound other than compound (5).
• the uses of the compound having a siloxane structure obtained using compound (4) as an intermediate are not particularly limited, and examples thereof include a surfactant, a leveling agent, a surface treatment agent, an alignment agent, an antireflection agent, and a water repellent agent.
• the present invention includes a compound represented by formula (7).
• R, R 1 , R 2 , m, n, and L are the same as those of R, R 1 , R 2 , m, n, and L in formula (3), respectively.
• X2 represents a chlorine atom, a bromine atom, or an iodine atom.
• m is preferably an integer of 1 or more, more preferably an integer of 1 to 20, even more preferably an integer of 1 to 15, and particularly preferably an integer of 1 to 10.
• X2 is a chlorine atom, it is preferred that m satisfies the above preferred range.
• Examples of the compound represented by formula (7) include the compound represented by formula (3) and the compound represented by formula (4) described above.
• Compound D-4 was synthesized in the same manner as in the above-mentioned [Synthesis of Compound D-3], except that Compound A-2 was replaced with Compound A-3 and Compound B-3 was replaced with Compound B-4.
• the results of 1 H NMR measurement of Compound D-4 are shown below.
• Compound D-5 was synthesized in the same manner as in the above-mentioned [Synthesis of Compound D-3], except that Compound A-2 was replaced with Compound A-4 and Compound B-3 was replaced with Compound B-5.
• the 1 H NMR measurement results of Compound D-5 are shown below. 1H NMR (400MHz, CDCl3 ) ⁇ ppm: 0.05-0.09 (m, 63H), 0.56-0.61 (m, 2H), 1.80-1.87 (m, 2H), 4.00 (t, 2H), 6.98 (d, 2H), 7.82 (d, 2H), 9.87 (s, 1H)
• Compound D-6 was synthesized in the same manner as in the above-mentioned [Synthesis of Compound D-3], except that Compound A-2 was replaced with Compound A-5 and Compound B-3 was replaced with Compound B-5.
• the results of 1 H NMR measurement of Compound D-6 are shown below. 1H NMR (400MHz, CDCl3 ) ⁇ ppm: 0.06-0.10 (m, 33H), 0.56-0.61 (m, 2H), 1.80-1.87 (m, 2H), 4.00 (t, 2H), 6.98 (d, 2H), 7.82 (d, 2H), 9.87 (s, 1H)

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