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US4147708A
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Preparation of carotenoids using a π-allyl complex
Assignee: Hoffmann La Roche Inc
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Filing: 1977-05-02
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Granted: 1979-04-03
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Expires: 1997-05-02
Abstract
Abstract A novel procedure for the preparation of carotenoids, particularly vitamin A, employing π-allyl transition metal complexes. Novel carotenoid intermediates are also disclosed.
Inventors
- 👤 Percy S. Manchand
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-01 13:02
CPC Classifications
C; C07; C07C; C07C403/00; C07C403/06; C07C403/08; C07C315/00; C07C315/04; C07C317/00; C07C317/16; C07C317/18; C07C403/12; C07C403/20; C07C57/00; C07C57/02; C07C57/03; C07C69/00; C07C69/02; C07C69/12; C07C69/14; C07C69/145; C07C2601/00; C07C2601/12; C07C2601/16
Claims Analysis
Total Claims: 15
Claim 1
Independent Claim
159 words
A process for the preparation of a compound of the formula ##STR20## wherein R is ##STR21## R 1 is --CH 2 OH, or ##STR22## R 2 and R 3 are lower alkyl the dotted line is a carbon-carbon bond which may be in either the 4,5 or 5,6 position; which comprises reacting a compound of the formula ##STR23## wherein M is Pd or Pt, X is halogen; with a compound of the formula R.sub.4 --CH.sub.2 SO.sub.2 R.sub.5 wherein R 4 is ##STR24## and R 5 is lower alkyl, aryl or lower alkylaryl and the dotted line is a carbon to carbon bond in either the 4,5 or 5,6 position; under basic conditions in the presence of a ligand or a solvent capable of coordinating with the platinum or palladium to form a compound having the formula ##STR25## wherein R 1 , R 4 and R 5 are as defined above followed by treatment of said compound with a base.
Claim 2
Dependent Claim
159 words
A process for the preparation of a compound of the formula ##STR20## wherein R is ##STR21## R 1 is --CH 2 OH, or ##STR22## R 2 and R 3 are lower alkyl the dotted line is a carbon-carbon bond which may be in either the 4,5 or 5,6 position; which comprises reacting a compound of the formula ##STR23## wherein M is Pd or Pt, X is halogen; with a compound of the formula R.sub.4 --CH.sub.2 SO.sub.2 R.sub.5 wherein R 4 is ##STR24## and R 5 is lower alkyl, aryl or lower alkylaryl and the dotted line is a carbon to carbon bond in either the 4,5 or 5,6 position; under basic conditions in the presence of a ligand or a solvent capable of coordinating with the platinum or palladium to form a compound having the formula ##STR25## wherein R 1 , R 4 and R 5 are as defined above followed by treatment of said compound with a base.
Claim 3
Dependent Claim
22 words
The process of claim 1 wherein R 4 is ##STR26## R 5 is phenyl, M is Pd and the halogen is chlorine.
Claim 4
Dependent Claim
18 words
The process of claim 2 wherein the reaction is conducted in the presence of an optically inactive ligand.
Claim 5
Dependent Claim
10 words
The process of claim 3 wherein said ligand is triphenylphosphine.
Claim 6
Dependent Claim
13 words
The process of claim 1 wherein said base is an alkali metal alkoxide.
Claim 7
Dependent Claim
13 words
The process of claim 5 wherein said alkali metal alkoxide is sodium ethoxide.
Claim 8
Dependent Claim
22 words
The process of claim 1 wherein R 4 is ##STR27## R 5 is phenyl, M is Pd and the halogen is chlorine.
Claim 9
Dependent Claim
18 words
The process of claim 7 wherein the reaction is conducted in the presence of an optically inactive ligand.
Claim 10
Dependent Claim
10 words
The process of claim 8 wherein said ligand is triphenylphosphine.
Claim 11
Dependent Claim
26 words
The process of claim 1 wherein R 4 is ##STR28## R 2 is methyl, R 5 is phenyl, M is Pd and the halogen is chlorine.
Claim 12
Dependent Claim
18 words
The process of claim 10 wherein the reaction is conducted in the presence of an optically inactive ligand.
Claim 13
Dependent Claim
10 words
The process of claim 11 wherein said ligand is triphenylphosphine.
Claim 14
Dependent Claim
201 words
A process for the preparation of a compound of the formula ##STR29## and R 2 is lower alkyl; the dotted line is a carbon-carbon bond which may be in either the 4,5 or 5,6 position; which comprises reacting a compound of the formula ##STR30## wherein M is Pd or Pt, and X is halogen; with a compound of the formula R.sub.4 --CH.sub.2 SO.sub.2 R.sub.5 wherein R 4 is ##STR31## and R 5 is lower alkyl, aryl or lower alkylaryl and the dotted line is a carbon to carbon bond in either the 4,5 or 5,6 position; in the presence of a base selected from the group consisting of alkali metal lower alkoxides, hydrides and amides in the presence of a ligand selected from mono-, di- or tri-substituted amines, arsines, or phosphines wherein said substitutents are lower alkyl, aryl or lower alkylaryl or a solvent capable of coordinating with the platinum or palladium selected from dimethylsulfoxide or hexamethylphosphoramide to form a compound having the formula ##STR32## wherein R 4 and R 5 are as defined above followed by treatment of said compound with a base selected from alkali metal hydroxide or a mixture of a lower alkanol and an alkali metal hydroxide.
Claim 15
Dependent Claim
201 words
A process for the preparation of a compound of the formula ##STR29## and R 2 is lower alkyl; the dotted line is a carbon-carbon bond which may be in either the 4,5 or 5,6 position; which comprises reacting a compound of the formula ##STR30## wherein M is Pd or Pt, and X is halogen; with a compound of the formula R.sub.4 --CH.sub.2 SO.sub.2 R.sub.5 wherein R 4 is ##STR31## and R 5 is lower alkyl, aryl or lower alkylaryl and the dotted line is a carbon to carbon bond in either the 4,5 or 5,6 position; in the presence of a base selected from the group consisting of alkali metal lower alkoxides, hydrides and amides in the presence of a ligand selected from mono-, di- or tri-substituted amines, arsines, or phosphines wherein said substitutents are lower alkyl, aryl or lower alkylaryl or a solvent capable of coordinating with the platinum or palladium selected from dimethylsulfoxide or hexamethylphosphoramide to form a compound having the formula ##STR32## wherein R 4 and R 5 are as defined above followed by treatment of said compound with a base selected from alkali metal hydroxide or a mixture of a lower alkanol and an alkali metal hydroxide.
References Cited (Backward Citations)
US3876673A
Cited
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1982-04-02 | 1982-10-02 | 1983-04-03 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1986-04-02 | 1986-10-02 | 1987-04-03 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1990-04-02 | 1990-10-02 | 1991-04-03 | $7700.00 | Window Closed / Lapsed |