FR2419939A1 - Procede de preparation d'un ether d'alcool a-cyane optiquement actif - Google Patents
Procede de preparation d'un ether d'alcool a-cyane optiquement actifInfo
- Publication number
- FR2419939A1 FR2419939A1 FR7807779A FR7807779A FR2419939A1 FR 2419939 A1 FR2419939 A1 FR 2419939A1 FR 7807779 A FR7807779 A FR 7807779A FR 7807779 A FR7807779 A FR 7807779A FR 2419939 A1 FR2419939 A1 FR 2419939A1
- Authority
- FR
- France
- Prior art keywords
- cyane
- preparing
- optically active
- alcohol ether
- compound
- 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.)
- Granted
Links
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 title abstract 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 title 1
- 238000004519 manufacturing process Methods 0.000 title 1
- 229940126062 Compound A Drugs 0.000 abstract 3
- NLDMNSXOCDLTTB-UHFFFAOYSA-N Heterophylliin A Natural products O1C2COC(=O)C3=CC(O)=C(O)C(O)=C3C3=C(O)C(O)=C(O)C=C3C(=O)OC2C(OC(=O)C=2C=C(O)C(O)=C(O)C=2)C(O)C1OC(=O)C1=CC(O)=C(O)C(O)=C1 NLDMNSXOCDLTTB-UHFFFAOYSA-N 0.000 abstract 3
- QQZOPKMRPOGIEB-UHFFFAOYSA-N 2-Oxohexane Chemical compound CCCCC(C)=O QQZOPKMRPOGIEB-UHFFFAOYSA-N 0.000 abstract 2
- 241000039077 Copula Species 0.000 abstract 1
- 230000001476 alcoholic effect Effects 0.000 abstract 1
- 125000004093 cyano group Chemical group *C#N 0.000 abstract 1
- 239000000203 mixture Substances 0.000 abstract 1
- 239000002904 solvent Substances 0.000 abstract 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
- C07D307/77—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D307/93—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems condensed with a ring other than six-membered
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Furan Compounds (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Abstract
L'invention a pour objet un procédé de préparation du (1R, 5S) 6,6-diméthyl 4(R)/(S)cyano (3'-phénoxy phényl méthoxy/3-oxa bicyclo (3-1-0) hexan-2-one composé A consistant à faire agir, sur un mélange de composé A et de son éther diastéréo-isomère dans lequel la copule alcoolique est de configuration R, une base, au sein d'un solvant dans lequel le composé A est insoluble.
Priority Applications (18)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
FR7807779A FR2419939A1 (fr) | 1978-03-17 | 1978-03-17 | Procede de preparation d'un ether d'alcool a-cyane optiquement actif |
SE7900890D SE7900890L (sv) | 1978-03-17 | 1979-02-01 | Sett att framstella optisk aktiv (1r, 5s)6,6-dimetyl-4(r)-(s)-cyano-(3'-fenoxi-fenyl)-metoxi-3-oxa-bicyklo(3-1-0)hexan-2-on |
SE7900890A SE445218B (sv) | 1978-03-17 | 1979-02-01 | Sett att framstella optiskt aktiv (1r, 5s) 6,6-dimetyl-4(r)-/(s)-cyano-(3'-fenoxi-fenyl)-metoxi/-3-oxa-bicyklo(3-1-0)hexan-2-on |
HU79RO1012A HU178335B (en) | 1978-03-17 | 1979-03-06 | Process for preparing /ir,5s/6,6-dimethyl-4/r//s/-cyano/3'-phenoxy-phenyl-methoxy/- 3-oxa-bicyclo/3,1,0/hexan-2-one |
US06/018,308 US4206124A (en) | 1978-03-17 | 1979-03-07 | Epimerization process |
ZA791066A ZA791066B (en) | 1978-03-17 | 1979-03-07 | Process for preparing an optically active a-cyano alcohol ether |
ES478568A ES478568A1 (es) | 1978-03-17 | 1979-03-13 | Un procedimiento de preparacion de (1r.5s)-6,6-dimetil-4(r)--(s)-ciano-(3'-fenoxifenil)-metoxi-3-oxa-biciclo (3-1-0)- hexan-2-ona. |
IT48344/79A IT1114716B (it) | 1978-03-17 | 1979-03-14 | Procedimento per la produzione di un etere di alfa-ciano-alcool otticamente attivo |
DK108779A DK160988C (da) | 1978-03-17 | 1979-03-16 | Fremgangsmaade til fremstilling af (1r,5s)-6,6-dimethyl-4(r)-((s)-cyan-(3'-phenoxyphenyl)-methoxy)-3-oxabicyclo(3.1.0)hexan-2-on |
BE0/194058A BE874893A (fr) | 1978-03-17 | 1979-03-16 | Procede de preparation d'un ether d'alcool alpha-cyane optiquement actif |
CH253179A CH636868A5 (fr) | 1978-03-17 | 1979-03-16 | Procede de preparation d'un ether d'alcool alpha-cyane optiquement actif. |
NLAANVRAGE7902117,A NL189260C (nl) | 1978-03-17 | 1979-03-16 | Werkwijze voor de bereiding van (1r,5s) 6,6-dimethyl 4(r) ((s)-cyaan-(3'-fenoxyfenyl)methoxy)-3-oxabicyclo(3,1,0)-hexanon-2. |
GB7909328A GB2016459B (en) | 1978-03-17 | 1979-03-16 | Process for the preparation of an optically active -cyano alcohol ether |
JP3009979A JPS54130557A (en) | 1978-03-17 | 1979-03-16 | Manufacture of photoactive alphaacyanoalcohol ether |
DE19792910417 DE2910417A1 (de) | 1978-03-17 | 1979-03-16 | Verfahren zur herstellung eines optisch aktiven alpha -cyanoalkoholaethers |
AU45178/79A AU520059B2 (en) | 1978-03-17 | 1979-03-16 | "3-oxa bicyclo (3-1-0) hexan-2-one derivatives |
CA323,659A CA1128059A (fr) | 1978-03-17 | 1979-03-16 | PROCEDE DE PREPARATION D'UN ETHER D'ALCOOL .alpha.-CYANE OPTIQUEMENT ACTIF |
IE731/79A IE47819B1 (en) | 1978-03-17 | 1979-08-08 | Process for the preparation of an optically active alpha-cyano alcohol ether |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
FR7807779A FR2419939A1 (fr) | 1978-03-17 | 1978-03-17 | Procede de preparation d'un ether d'alcool a-cyane optiquement actif |
Publications (2)
Publication Number | Publication Date |
---|---|
FR2419939A1 true FR2419939A1 (fr) | 1979-10-12 |
FR2419939B1 FR2419939B1 (fr) | 1980-11-28 |
Family
ID=9205945
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
FR7807779A Granted FR2419939A1 (fr) | 1978-03-17 | 1978-03-17 | Procede de preparation d'un ether d'alcool a-cyane optiquement actif |
Country Status (17)
Country | Link |
---|---|
US (1) | US4206124A (fr) |
JP (1) | JPS54130557A (fr) |
AU (1) | AU520059B2 (fr) |
BE (1) | BE874893A (fr) |
CA (1) | CA1128059A (fr) |
CH (1) | CH636868A5 (fr) |
DE (1) | DE2910417A1 (fr) |
DK (1) | DK160988C (fr) |
ES (1) | ES478568A1 (fr) |
FR (1) | FR2419939A1 (fr) |
GB (1) | GB2016459B (fr) |
HU (1) | HU178335B (fr) |
IE (1) | IE47819B1 (fr) |
IT (1) | IT1114716B (fr) |
NL (1) | NL189260C (fr) |
SE (2) | SE445218B (fr) |
ZA (1) | ZA791066B (fr) |
Families Citing this family (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE2326077C2 (de) * | 1972-05-25 | 1985-12-12 | National Research Development Corp., London | Ungesättigte Cyclopropancarbonsäuren und deren Derivate, deren Herstellung und diese enthaltende Insektizide |
FR2423488A1 (fr) * | 1978-03-17 | 1979-11-16 | Roussel Uclaf | Nouveaux ethers dont les restes organiques comportent des atomes chiraux, leur procede de preparation et leur application au dedoublement des alcools, des phenols ou de certains composes de structure lactonique |
FR2472570A1 (fr) * | 1979-07-31 | 1981-07-03 | Roussel Uclaf | Procede de preparation du (1,5) 6,6-dimethyl 4-hydroxy 3-oxa bicylo(3.1.0.)hexan-2-one et de ses ethers en position 4, sous toutes leurs formes stereoisomeres |
FR2471377A1 (fr) * | 1979-12-10 | 1981-06-19 | Roussel Uclaf | Nouveaux composes comportant un groupement azote, leur procede de preparation et leur application au dedoublement de certains composes organiques |
US4276230A (en) * | 1980-04-21 | 1981-06-30 | Zoecon Corporation | Cyano-3-phenoxybenzyl N-1-(1-naphthyl) ethylcarbamate |
Citations (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE2718039A1 (de) * | 1976-04-23 | 1977-11-17 | Roussel Uclaf | Verfahren zur umwandlung eines esters einer chiralen saeure mit einem optisch aktiven sekundaeren alpha-cyanoalkohol der struktur (r) in einen ester einer chiralen saeure mit einem sekundaeren alpha- cyanoalkohol der struktur (s), produkte und insektizide mittel |
Family Cites Families (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4014918A (en) * | 1968-07-12 | 1977-03-29 | Roussel-Uclaf | Process for the preparation of cyclopropane derivatives and compounds produced therein |
FR2036088A5 (fr) * | 1969-03-04 | 1970-12-24 | Roussel Uclaf | |
US3922286A (en) * | 1971-03-23 | 1975-11-25 | Sumitomo Chemical Co | Process for the production of optically active dihydrochrysanthemolactone |
US3989654A (en) * | 1973-11-22 | 1976-11-02 | Sumitomo Chemical Company, Limited | Process for preparing cis-chrysanthemic acid |
US4132717A (en) * | 1977-08-09 | 1979-01-02 | Shell Oil Company | Enol lactone intermediate for the preparation of (1R,cis)-caronaldehydic acid |
ZA7911B (en) * | 1978-01-31 | 1980-01-30 | Roussel Uclaf | Optically-active substituted benzyl alcohol and process for preparing it |
-
1978
- 1978-03-17 FR FR7807779A patent/FR2419939A1/fr active Granted
-
1979
- 1979-02-01 SE SE7900890A patent/SE445218B/sv not_active IP Right Cessation
- 1979-02-01 SE SE7900890D patent/SE7900890L/xx not_active Application Discontinuation
- 1979-03-06 HU HU79RO1012A patent/HU178335B/hu not_active IP Right Cessation
- 1979-03-07 US US06/018,308 patent/US4206124A/en not_active Expired - Lifetime
- 1979-03-07 ZA ZA791066A patent/ZA791066B/xx unknown
- 1979-03-13 ES ES478568A patent/ES478568A1/es not_active Expired
- 1979-03-14 IT IT48344/79A patent/IT1114716B/it active
- 1979-03-16 AU AU45178/79A patent/AU520059B2/en not_active Expired
- 1979-03-16 CH CH253179A patent/CH636868A5/fr not_active IP Right Cessation
- 1979-03-16 DE DE19792910417 patent/DE2910417A1/de active Granted
- 1979-03-16 JP JP3009979A patent/JPS54130557A/ja active Granted
- 1979-03-16 NL NLAANVRAGE7902117,A patent/NL189260C/xx not_active IP Right Cessation
- 1979-03-16 CA CA323,659A patent/CA1128059A/fr not_active Expired
- 1979-03-16 GB GB7909328A patent/GB2016459B/en not_active Expired
- 1979-03-16 BE BE0/194058A patent/BE874893A/fr not_active IP Right Cessation
- 1979-03-16 DK DK108779A patent/DK160988C/da active
- 1979-08-08 IE IE731/79A patent/IE47819B1/en not_active IP Right Cessation
Patent Citations (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE2718039A1 (de) * | 1976-04-23 | 1977-11-17 | Roussel Uclaf | Verfahren zur umwandlung eines esters einer chiralen saeure mit einem optisch aktiven sekundaeren alpha-cyanoalkohol der struktur (r) in einen ester einer chiralen saeure mit einem sekundaeren alpha- cyanoalkohol der struktur (s), produkte und insektizide mittel |
Also Published As
Publication number | Publication date |
---|---|
NL189260C (nl) | 1993-02-16 |
DK108779A (da) | 1979-09-18 |
ES478568A1 (es) | 1979-05-16 |
JPS6221787B2 (fr) | 1987-05-14 |
DE2910417A1 (de) | 1979-09-20 |
AU520059B2 (en) | 1982-01-14 |
BE874893A (fr) | 1979-09-17 |
SE445218B (sv) | 1986-06-09 |
AU4517879A (en) | 1979-09-20 |
US4206124A (en) | 1980-06-03 |
CA1128059A (fr) | 1982-07-20 |
IT7948344A0 (it) | 1979-03-14 |
DE2910417C2 (fr) | 1988-09-15 |
IE47819B1 (en) | 1984-06-27 |
NL7902117A (nl) | 1979-09-19 |
NL189260B (nl) | 1992-09-16 |
CH636868A5 (fr) | 1983-06-30 |
IE790731L (en) | 1979-09-17 |
IT1114716B (it) | 1986-01-27 |
HU178335B (en) | 1982-04-28 |
ZA791066B (en) | 1980-03-26 |
GB2016459A (en) | 1979-09-26 |
SE7900890L (sv) | 1979-09-18 |
DK160988C (da) | 1991-11-11 |
FR2419939B1 (fr) | 1980-11-28 |
GB2016459B (en) | 1982-09-15 |
JPS54130557A (en) | 1979-10-09 |
DK160988B (da) | 1991-05-13 |
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Legal Events
Date | Code | Title | Description |
---|---|---|---|
ST | Notification of lapse |