DE3514384A1 - Substituierte furane und deren vorprodukte - Google Patents
Substituierte furane und deren vorprodukteInfo
- Publication number
- DE3514384A1 DE3514384A1 DE19853514384 DE3514384A DE3514384A1 DE 3514384 A1 DE3514384 A1 DE 3514384A1 DE 19853514384 DE19853514384 DE 19853514384 DE 3514384 A DE3514384 A DE 3514384A DE 3514384 A1 DE3514384 A1 DE 3514384A1
- Authority
- DE
- Germany
- Prior art keywords
- hydrogen
- hydroxyalkyl
- protective group
- alkoxycarbonyl
- furans
- 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.)
- Withdrawn
Links
- 150000002240 furans Chemical class 0.000 title claims abstract description 6
- 239000002243 precursor Chemical class 0.000 title description 2
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 7
- 239000001257 hydrogen Substances 0.000 claims abstract description 7
- 125000006239 protecting group Chemical group 0.000 claims abstract description 5
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 4
- 238000002360 preparation method Methods 0.000 claims abstract description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 3
- 150000002367 halogens Chemical group 0.000 claims abstract description 3
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims abstract 4
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims abstract 3
- 125000001188 haloalkyl group Chemical group 0.000 claims abstract 3
- 125000003545 alkoxy group Chemical group 0.000 claims abstract 2
- 125000003710 aryl alkyl group Chemical group 0.000 claims abstract 2
- 125000003118 aryl group Chemical group 0.000 claims abstract 2
- 125000004093 cyano group Chemical group *C#N 0.000 claims abstract 2
- 125000004438 haloalkoxy group Chemical group 0.000 claims abstract 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims abstract 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 7
- WEQPBCSPRXFQQS-UHFFFAOYSA-N 4,5-dihydro-1,2-oxazole Chemical compound C1CC=NO1 WEQPBCSPRXFQQS-UHFFFAOYSA-N 0.000 claims description 5
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 4
- 238000000034 method Methods 0.000 claims description 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 3
- 125000005843 halogen group Chemical group 0.000 claims 1
- 125000000217 alkyl group Chemical group 0.000 abstract 1
- 150000002431 hydrogen Chemical class 0.000 abstract 1
- 238000005984 hydrogenation reaction Methods 0.000 abstract 1
- 150000002547 isoxazolines Chemical class 0.000 abstract 1
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 4
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- GYIYRRFHDPWBNJ-UHFFFAOYSA-N (3-butan-2-yl-1,2-oxazol-5-yl)methyl acetate Chemical compound CCC(C)C=1C=C(COC(C)=O)ON=1 GYIYRRFHDPWBNJ-UHFFFAOYSA-N 0.000 description 2
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- SEWWFHKIKWFJNV-GQCTYLIASA-N (E)-2-methylbutanal oxime Chemical compound CCC(C)\C=N\O SEWWFHKIKWFJNV-GQCTYLIASA-N 0.000 description 1
- FITPKMAKSVCPDP-UHFFFAOYSA-N 2-butan-2-ylfuran Chemical group CCC(C)C1=CC=CO1 FITPKMAKSVCPDP-UHFFFAOYSA-N 0.000 description 1
- 239000007832 Na2SO4 Substances 0.000 description 1
- 239000007868 Raney catalyst Substances 0.000 description 1
- NPXOKRUENSOPAO-UHFFFAOYSA-N Raney nickel Chemical compound [Al].[Ni] NPXOKRUENSOPAO-UHFFFAOYSA-N 0.000 description 1
- 229910000564 Raney nickel Inorganic materials 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-N carbonic acid Chemical compound OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- HVAMZGADVCBITI-UHFFFAOYSA-M pent-4-enoate Chemical compound [O-]C(=O)CCC=C HVAMZGADVCBITI-UHFFFAOYSA-M 0.000 description 1
- 239000011814 protection agent Substances 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
- C07D307/34—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D307/38—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D307/40—Radicals substituted by oxygen atoms
- C07D307/42—Singly bound oxygen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/56—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds from heterocyclic compounds
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D261/00—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings
- C07D261/02—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings not condensed with other rings
- C07D261/04—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
- C07D307/34—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D307/56—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D307/68—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen
-
- 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
- C07F9/6527—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having nitrogen and oxygen atoms as the only ring hetero atoms
- C07F9/653—Five-membered rings
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/55—Design of synthesis routes, e.g. reducing the use of auxiliary or protecting groups
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)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
Description
-
- Substituierte Furane und deren Vorprodukte
- Zusatz zu Patent .. .. ... (Patentanmeldung P 34 47 793.4).
- Bis ZU vierfach substituierte Furane der allgemeinen Formel (I) in der R1 bis R4 die in den vorstehenden Ansprüchen angegebene Bedeutung haben, werden als Vorprodukte, z.B. für die Herstellung von Pflanzenschutzmitteln benötigt.
- Es wurde nun gefunden, daß man Furane der vorgenannten Art, bei denen R1 oder R3 Wasserstoff ist. vorteilhaft dadurch erhält, daB man ein entsprechendes Isoxazolin der Formel II in der X Hydroxy, Halogen oder durch eine abspaltbare Schutzgruppe verkappter Hydroxy bedeutet, nach dem Verfahren des Hauptpatents hydriert.
- Abhängig von der speziellen Verfahrensweise kann dies direkt geschehen oder es kann als Zwischenstufe das Hydroxyketon III isoliert und in einem anschließenden Schritt das gewünschte Furan I erhalten werden: Zur Herstellung der benötigten tsoxazoline II ist insbesondere das folgende zu sagen: Isoxazoline II mit der Bedeutung von R3 : Wasserstoff konnen z.B. nach der Methode in Grundman, Grunanger, The Nitrile Oxides 1. Aufl. 1971, 5. 96 ff erhalten werden nach Für R1 = Wasserstoff ist ebenfalls ein Herstellverfahren beschrieben: Huisgen und Christl, Angew. Chem. 79 S. 471/472 (1967).
- Herstellungsbeispiel für ein Isoxazolin Zu 200 g Allylacetat und 242 g 2-Methylbutyraldoxim in 600 g Methylenchlorid werden 1960 g 10 %ige NaOH-Lõsung nach und nach zugegeben und 3 Stunden bei Raumtemperatur gerührt. Die organische Phase wird abgetrennt. mit Wasser gewaschen, über Na2SO4 getrocknet und nach Filtration vom Lösungsmittel befreit. Das zurückbleibende Öl (339 91 ist 3-sec.Butyl-5-acetoxymethyl-isoxazol.
- 300-MHz-NMR-Spektrum in CDCl3 (ppm): 0,95 (3H); 1,08 (3H); 1,2-1,3 (2H); 2,04 (3H); 2,3 (1H); 2,35 (1H); 3,0 (1H); 4,0-4,1 (2H); 4,4 (1H).
- Herstellungsbeispiel für ein Furan 100 g 3-sec.Butyl-5-acetoxymethylisoxazol in 400 g Methanol und 27 g Wasser werden mit 25 g Raney-Nickel bei 20-30° hydriert. Danach wird filtriert, vom Losungsmittel befreit und destilliert. Die bei 70-800C überdestillierende Flüssigkeit ist 2-sec.Butyl-furan. 200 MHz-NMR-Spektrum in CDCl3 Ippm): 0,9 (3H); 1,25 (2H); 1,5-1,8 (2H); 2,78 (1H); 6,0 11H); 6,3 (1H); 7,35 (1H).
Claims (1)
- Patentanspruch Verfahren zur Herstellung von Furanen der allgemeinen Formel I, wobei man ein Isoxazolin der allgemeinen Formel II in der R1, R2, R3 und R4 unsubstituiertes oder durch Halogen, Haloalkyl, Alkoxy, Haloalkoxy, Nitro, Cyano, Dialkylphosphonyl oder Alkoxycarbonyl substituiertes Alkyl, Aryl. Aralkyl, Alkoxycarbonyl oder Dialkoxyphosphoyl, R2 und R4 auch Wasserstoff und R3 auch Hydroxyalkyl oder durch eine abspaltbare Schutzgruppe verkapptes Hydroxyalkyl, X Hydroxy, Halogen oder durch eine abspaltbare Schutzgruppe verkapptes Hydroxy bedeutet. hydriert nach Patent .. .. .. (Patentanmeldung P 34 47 793.4), dadurch gekennzeichnet. daß man ein Isoxazolin II hyhydriert bei dem R1 oder R3 Wasserstoff bedeutet und ein entsprechendes Furan (1) gewinnt.
Priority Applications (10)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19853514384 DE3514384A1 (de) | 1985-04-20 | 1985-04-20 | Substituierte furane und deren vorprodukte |
| DE8585116323T DE3565103D1 (en) | 1984-12-29 | 1985-12-20 | Substituted furanes and their precursors |
| AT85116323T ATE37362T1 (de) | 1984-12-29 | 1985-12-20 | Substituierte furane und deren vorprodukte. |
| EP85116323A EP0187345B1 (de) | 1984-12-29 | 1985-12-20 | Substituierte Furane und deren Vorprodukte |
| AU51679/85A AU579693B2 (en) | 1984-12-29 | 1985-12-24 | Novel substituted isoxazolines as precursors for substituted furans |
| IL77448A IL77448A (en) | 1984-12-29 | 1985-12-25 | Preparation of substituted furans and novel isoxazolines used as starting materials therefor |
| HU854968A HUT39734A (en) | 1984-12-29 | 1985-12-27 | Process for preparing furan derivatives |
| CA000498662A CA1268465A (en) | 1984-12-29 | 1985-12-27 | Isoxazolines useful in preparing furans |
| DK608185A DK168335B1 (da) | 1984-12-29 | 1985-12-30 | Fremgangsmåde til fremstilling af substituerede furanforbindelser og isoxazoliner til brug herved |
| US07/384,910 US4954633A (en) | 1984-12-29 | 1989-07-25 | Isoxazolines as intermediates to furans |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19853514384 DE3514384A1 (de) | 1985-04-20 | 1985-04-20 | Substituierte furane und deren vorprodukte |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE3514384A1 true DE3514384A1 (de) | 1986-10-23 |
Family
ID=6268737
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19853514384 Withdrawn DE3514384A1 (de) | 1984-12-29 | 1985-04-20 | Substituierte furane und deren vorprodukte |
Country Status (1)
| Country | Link |
|---|---|
| DE (1) | DE3514384A1 (de) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4954633A (en) * | 1984-12-29 | 1990-09-04 | Basf Aktiengesellschaft | Isoxazolines as intermediates to furans |
-
1985
- 1985-04-20 DE DE19853514384 patent/DE3514384A1/de not_active Withdrawn
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4954633A (en) * | 1984-12-29 | 1990-09-04 | Basf Aktiengesellschaft | Isoxazolines as intermediates to furans |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| DE1941536A1 (de) | 1-Alkyl-2-aminomethylpyrrolidine sowie Verfahren zur Herstellung dieser Verbindungen und deren Zwischenprodukte | |
| DE1122075B (de) | Verfahren zur Herstellung von Aminoaryl-(thio)-phosphorsaeure-Derivaten | |
| DE3514384A1 (de) | Substituierte furane und deren vorprodukte | |
| DE1543809A1 (de) | Verfahren zur Herstellung von Aminoverbindungen | |
| DE960813C (de) | Verfahren zur Herstellung von ungesaettigten ª†- und ª€-Laktonen | |
| DE3819438A1 (de) | Verfahren zur herstellung von optisch aktiven 1-arylethylaminen | |
| DE2507576A1 (de) | Verfahren zur herstellung eines n-substituierten pyrrolidons | |
| DE702894C (de) | Verfahren zur Herstellung von Oxyketonen | |
| EP0340708B1 (de) | Verfahren zur Herstellung von 3-(3,4,5,6-Tetrahydrophthalimido)-benzaldehyden | |
| AT240349B (de) | Verfahren zur Herstellung von 1, 5-disubstituierten 3-Azapentan-1-olen | |
| DE1279026B (de) | Verfahren zur Herstellung von 1-Hydroxy-2-naphthamidderivaten | |
| DE1807494C3 (de) | Optisch aktive ß-Brom-alkylisocyanate und Verfahren zu ihrer Herstellung | |
| DE959097C (de) | Verfahren zur Herstellung von basisch substituierten Diarylacetonitrilen | |
| DE957842C (de) | Verfahren zur Herstellung von neuen Octahydropyridopyrimidinverbindungen | |
| DE1445895C (de) | Verfahren zur Herstellung von 2 Dehydroemetinderivaten | |
| DE2159919A1 (de) | Verfahren zur Herstellung von Derivaten des 5-Phenyl-3H-l,4-benzodiazepins | |
| DE1795325C3 (de) | 3,3-Dialkyl-tetrahydro-chinoxaline sowie ein Verfahren zu deren Herstellung | |
| DE1272286C2 (de) | Verfahren zur Herstellung von N-substituierten aliphatischen Thiocarbonsaeureamiden | |
| DE2114251A1 (de) | Tertiaere Aminomethylderivate des N-Hydroxymethyl-2-pyrrolidinon und Verfahren zu deren Herstellung | |
| AT243268B (de) | Verfahren zur Herstellung von neuen Benzochinolizin-Derivaten | |
| CH539055A (de) | Verfahren zur Herstellung von 1,2,3,4-Tetrahydro-4-oxochinazolinen | |
| DE934824C (de) | Verfahren zur Herstellung von Alkoxyvinylmethylketonen | |
| AT251560B (de) | Verfahren zur Herstellung von neuen Phenylisopropylaminen und deren Salzen | |
| EP0492347A1 (de) | Verfahren zur Herstellung von threo-4-Alkoxy-5-(arylhydroxymethyl)-2(5H)-furanonen | |
| DE1948537B2 (de) | Verfahren zur herstellung von 3,3,4-trifluoroxetanen |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| AF | Is addition to no. |
Ref country code: DE Ref document number: 3447793 Format of ref document f/p: P |
|
| 8130 | Withdrawal |