US3682970A
Expired / Lapsed
US
⏱️ 0.0 years remaining
Production of unsaturated carbocyclic ketones
Assignee: Roche Palo Alto LLC
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Filing: 1969-03-27
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Granted: 1972-08-08
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Expires: 1989-03-27
Abstract
Abstract Preparation of Alpha , Beta -unsaturated carbocyclic ketones by reacting a methylene or methine phosphonium ylid with a delta keto carboxylic acid ester, anhydride or acyl halide. The reaction is useful for producing intermediates for synthesis of known steroids having estrogenic, progestational, or anabolic activity, for example.
Inventors
- 👤 Clive A Henrick
- 👤 John A Edwards
- 👤 John H Fried
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-27 08:27
CPC Classifications
C; C07; C07D; C07D317/00; C07D317/08; C07D317/72; C07C; C07C45/00; C07C45/45; C07C47/00; C07C47/02; C07C47/14; C07C51/00; C07C51/16; C07C51/21; C07C59/00; C07C59/40; C07C59/76; C07C59/80; C07C59/82; C07F; C07F9/00; C07F9/02; C07F9/28; C07F9/535; C07F9/5352; C07F9/54; C07C2603/00; C07C2603/02; C07C2603/04; C07C2603/06; C07C2603/10; C07C2603/12; C07C2603/16
Claims Analysis
Total Claims: 6
Claim 1
Independent Claim
62 words
The process of claim 9 wherein the methylene phosphonium ylid has the formula wherein R4 is lower alkyl, tetrahydropyran-2''-yl, tetrahydrofuran-2''-yl or 4''-methoxytetrahydropyran-4''-yl group, R5 is hydrogen or lower alkoxy, R6 is hydrogen or methyl, and each of R1, R2 and R3 is selected from the group consisting of substituted and unsubstituted, saturated and unsaturated, aliphatic and carbocyclic radicals and lower alkoxy radicals.
Claim 2
Dependent Claim
20 words
The process of claim 1 wherein the methylene phosphonium ylid is selected from the group of compounds having the formulas
Claim 3
Dependent Claim
55 words
The process of claim 1 including the step of adding a lower monohydric aliphatic alcohol and an alkali metal alkoxide or alkaline earth metal alkoxide base to the reaction mixture subsequent to the substantial disappearance of said ylid, and thereafter the reaction mixture is maintained at a temperature of from room temperature to reflux temperature.
Claim 4
Dependent Claim
43 words
The process of claim 1 including the step of adding a dipolar aprotic solvent to the reaction mixture subsequent to the substantial disappearance of said ylid, and thereafter the reaction mixture is maintained at a temperature of from room temperature to reflux temperature.
Claim 5
Dependent Claim
22 words
The process of claim 5 wherein the dipolar aprotic solvent is hexamethylphosphoramide, and thereafter the reaction mixture is maintained at reflux temperature.
Claim 6
Dependent Claim
20 words
The process of claim 3 wherein said organic solvent is diglyme, and the reaction mixture is maintained at reflux temperature.
References Cited (Backward Citations)
US3472885A
Cited
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1975-08-08 | 1976-02-07 | 1976-08-08 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1979-08-08 | 1980-02-07 | 1980-08-08 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1983-08-08 | 1984-02-07 | 1984-08-08 | $7700.00 | Window Closed / Lapsed |