ES367106A1 - Preparation of (cis-1,2-epoxypropyl)phosphonic acid and its salts and esters - Google Patents
Preparation of (cis-1,2-epoxypropyl)phosphonic acid and its salts and estersInfo
- Publication number
- ES367106A1 ES367106A1 ES367106A ES367106A ES367106A1 ES 367106 A1 ES367106 A1 ES 367106A1 ES 367106 A ES367106 A ES 367106A ES 367106 A ES367106 A ES 367106A ES 367106 A1 ES367106 A1 ES 367106A1
- Authority
- ES
- Spain
- Prior art keywords
- ethylide
- alkyl
- phosphonic acid
- epoxypropyl
- cis
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired
Links
- 150000002148 esters Chemical class 0.000 title abstract 3
- 150000003839 salts Chemical class 0.000 title abstract 3
- ABLZXFCXXLZCGV-UHFFFAOYSA-N Phosphorous acid Chemical compound OP(O)=O ABLZXFCXXLZCGV-UHFFFAOYSA-N 0.000 title abstract 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 abstract 4
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 abstract 3
- -1 diaryl sulphonium Chemical compound 0.000 abstract 3
- 229960001760 dimethyl sulfoxide Drugs 0.000 abstract 3
- 239000000243 solution Substances 0.000 abstract 3
- DEBRGDVXKPMWQZ-UHFFFAOYSA-N Formylphosphonate Chemical compound OP(O)(=O)C=O DEBRGDVXKPMWQZ-UHFFFAOYSA-N 0.000 abstract 2
- IJOOHPMOJXWVHK-UHFFFAOYSA-N chlorotrimethylsilane Chemical compound C[Si](C)(C)Cl IJOOHPMOJXWVHK-UHFFFAOYSA-N 0.000 abstract 2
- 150000001875 compounds Chemical class 0.000 abstract 2
- LJSQFQKUNVCTIA-UHFFFAOYSA-N diethyl sulfide Chemical compound CCSCC LJSQFQKUNVCTIA-UHFFFAOYSA-N 0.000 abstract 2
- CCAFPWNGIUBUSD-UHFFFAOYSA-N diethyl sulfoxide Chemical compound CCS(=O)CC CCAFPWNGIUBUSD-UHFFFAOYSA-N 0.000 abstract 2
- 230000007062 hydrolysis Effects 0.000 abstract 2
- 238000006460 hydrolysis reaction Methods 0.000 abstract 2
- LGRLWUINFJPLSH-UHFFFAOYSA-N methanide Chemical compound [CH3-] LGRLWUINFJPLSH-UHFFFAOYSA-N 0.000 abstract 2
- 239000002904 solvent Substances 0.000 abstract 2
- 125000006729 (C2-C5) alkenyl group Chemical group 0.000 abstract 1
- CBQVCYSLMQUWJA-UHFFFAOYSA-M 1-[diethyl(keto)sulfuraniumyl]ethane;iodide Chemical compound [I-].CC[S+](=O)(CC)CC CBQVCYSLMQUWJA-UHFFFAOYSA-M 0.000 abstract 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 abstract 1
- QXNVGIXVLWOKEQ-UHFFFAOYSA-N Disodium Chemical class [Na][Na] QXNVGIXVLWOKEQ-UHFFFAOYSA-N 0.000 abstract 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 abstract 1
- 239000002253 acid Substances 0.000 abstract 1
- 229910052783 alkali metal Inorganic materials 0.000 abstract 1
- 150000001340 alkali metals Chemical class 0.000 abstract 1
- 229910052784 alkaline earth metal Inorganic materials 0.000 abstract 1
- 125000000217 alkyl group Chemical group 0.000 abstract 1
- 239000007864 aqueous solution Substances 0.000 abstract 1
- 125000003118 aryl group Chemical group 0.000 abstract 1
- 239000002585 base Substances 0.000 abstract 1
- RDHPKYGYEGBMSE-UHFFFAOYSA-N bromoethane Chemical compound CCBr RDHPKYGYEGBMSE-UHFFFAOYSA-N 0.000 abstract 1
- 229910052791 calcium Inorganic materials 0.000 abstract 1
- 239000011575 calcium Substances 0.000 abstract 1
- 238000007327 hydrogenolysis reaction Methods 0.000 abstract 1
- 238000011065 in-situ storage Methods 0.000 abstract 1
- 229910052500 inorganic mineral Inorganic materials 0.000 abstract 1
- HVTICUPFWKNHNG-UHFFFAOYSA-N iodoethane Chemical compound CCI HVTICUPFWKNHNG-UHFFFAOYSA-N 0.000 abstract 1
- 239000007788 liquid Substances 0.000 abstract 1
- 238000000034 method Methods 0.000 abstract 1
- SNVLJLYUUXKWOJ-UHFFFAOYSA-N methylidenecarbene Chemical compound C=[C] SNVLJLYUUXKWOJ-UHFFFAOYSA-N 0.000 abstract 1
- 239000011707 mineral Substances 0.000 abstract 1
- NHKJPPKXDNZFBJ-UHFFFAOYSA-N phenyllithium Chemical compound [Li]C1=CC=CC=C1 NHKJPPKXDNZFBJ-UHFFFAOYSA-N 0.000 abstract 1
- XYFCBTPGUUZFHI-UHFFFAOYSA-O phosphonium Chemical compound [PH4+] XYFCBTPGUUZFHI-UHFFFAOYSA-O 0.000 abstract 1
- 239000000047 product Substances 0.000 abstract 1
- 239000000376 reactant Substances 0.000 abstract 1
- 229910052708 sodium Inorganic materials 0.000 abstract 1
- 239000011734 sodium Substances 0.000 abstract 1
- HSFQBFMEWSTNOW-UHFFFAOYSA-N sodium;carbanide Chemical group [CH3-].[Na+] HSFQBFMEWSTNOW-UHFFFAOYSA-N 0.000 abstract 1
- 239000006228 supernatant Substances 0.000 abstract 1
- HWCKGOZZJDHMNC-UHFFFAOYSA-M tetraethylammonium bromide Chemical compound [Br-].CC[N+](CC)(CC)CC HWCKGOZZJDHMNC-UHFFFAOYSA-M 0.000 abstract 1
- ZMANZCXQSJIPKH-UHFFFAOYSA-O triethylammonium ion Chemical compound CC[NH+](CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-O 0.000 abstract 1
- ANUSMYJRISPAKG-UHFFFAOYSA-M triethylsulfanium;bromide Chemical compound [Br-].CC[S+](CC)CC ANUSMYJRISPAKG-UHFFFAOYSA-M 0.000 abstract 1
- 239000005051 trimethylchlorosilane Substances 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C381/00—Compounds containing carbon and sulfur and having functional groups not covered by groups C07C301/00 - C07C337/00
- C07C381/12—Sulfonium compounds
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C381/00—Compounds containing carbon and sulfur and having functional groups not covered by groups C07C301/00 - C07C337/00
-
- 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
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/28—Phosphorus compounds with one or more P—C bonds
- C07F9/535—Organo-phosphoranes
- C07F9/5352—Phosphoranes containing the structure P=C-
-
- 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
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
- C07F9/655—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having oxygen atoms, with or without sulfur, selenium, or tellurium atoms, as the only ring hetero atoms
- C07F9/65502—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having oxygen atoms, with or without sulfur, selenium, or tellurium atoms, as the only ring hetero atoms the oxygen atom being part of a three-membered ring
- C07F9/65505—Phosphonic acids containing oxirane groups; esters thereof
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Biochemistry (AREA)
- General Health & Medical Sciences (AREA)
- Molecular Biology (AREA)
Abstract
(Cis-1,2-epoxypropyl)-phosphonic acid and its salts and esters are obtained by treating a formyl phosphonate, e.g. a compound in which R is a C 1 -C 5 alkyl, C 2 -C 5 alkenyl, aryl, or aralkyl radical with an ethylide which is substituted at the methylene carbon by an appropriate leaving group, i.e. a compound M#-CH#-CH 3 wherein M+ is the leaving group, e.g. a di-(C 1 -C 5 )- alkoxy phosphinyl, di-(C 1 -C 5 ) alkyl or diaryl sulphonium, tri-(C 1 -C 5 )-alkyl- (or triaryl) - ammonium, di-(C 1 -C 5 )-alkyl sulphoxonium, tri-(C 1 -C 5 )-alkyl phosphonium or triaryl phosphonium cation. The process is suitably conducted in a solvent, e.g. an ether or dimethylsulphoxide, and the ethylide reactant may be prepared in situ in the solvent and the formyl phosphonate then added to the solution. When the products are esters they may be converted to the free (cis-1,2-epoxypropyl)-phosphonic acid, e.g. by hydrolysis with a mineral acid, hydrogenolysis, or treatment with trimethylchlorosilane followed by -aqueous hydrolysis. The phosphonic acid may then be converted to a salt, e.g. an alkali metal or alkaline earth metal salt, especially the calcium or disodium salt, by treatment with an aqueous solution of an appropriate base. Diethyl sulphoxonium ethylide is obtained by reacting diethyl sulphoxide with ethyl iodide in solution at 100-110 C. to form triethylsulphoxonium iodide and then treating the latter with sodium methylsulphonyl methylide in dimethyl sulphoxide. Triethylammonium ethylide is obtained by adding tetraethylammonium bromide in ether to an ethereal solution of phenyl lithium at 25 C. and decanting the supernatant liquid. Diethylsulphonium ethylide is obtained by reacting diethyl sulphide with ethyl bromide to form triethylsulphonium bromide and then treating the latter with an equivalent of sodium methyl sulphonyl methylide in dimethylsulphoxide.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US72941568A | 1968-05-15 | 1968-05-15 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ES367106A1 true ES367106A1 (en) | 1971-06-16 |
Family
ID=24930926
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ES367106A Expired ES367106A1 (en) | 1968-05-15 | 1969-05-12 | Preparation of (cis-1,2-epoxypropyl)phosphonic acid and its salts and esters |
Country Status (8)
| Country | Link |
|---|---|
| BE (1) | BE733047A (en) |
| CH (1) | CH537954A (en) |
| DE (1) | DE1924264A1 (en) |
| ES (1) | ES367106A1 (en) |
| GB (1) | GB1246206A (en) |
| IL (1) | IL32135A0 (en) |
| NL (1) | NL6905269A (en) |
| SE (1) | SE362884B (en) |
-
1969
- 1969-04-01 SE SE04616/69A patent/SE362884B/xx unknown
- 1969-04-03 NL NL6905269A patent/NL6905269A/xx unknown
- 1969-05-01 IL IL32135A patent/IL32135A0/en unknown
- 1969-05-12 GB GB23985/69A patent/GB1246206A/en not_active Expired
- 1969-05-12 ES ES367106A patent/ES367106A1/en not_active Expired
- 1969-05-12 DE DE19691924264 patent/DE1924264A1/en active Pending
- 1969-05-14 BE BE733047D patent/BE733047A/xx unknown
- 1969-05-14 CH CH743069A patent/CH537954A/en not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| NL6905269A (en) | 1969-11-18 |
| IL32135A0 (en) | 1969-07-30 |
| BE733047A (en) | 1969-11-14 |
| CH537954A (en) | 1973-06-15 |
| GB1246206A (en) | 1971-09-15 |
| SE362884B (en) | 1973-12-27 |
| DE1924264A1 (en) | 1970-01-22 |
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