Methyl 2-(triphenyl-lambda~5~-phosphanylidene)propanoate → (E)-2,6-dimethyl-9-phenyl-2,6-nonadienoic acid methyl ester

HRID 470161Notes

Reaction equation

HRID 470161 reaction equation
[CH3:1][O:2][C:3](=[O:20])/[C:4](/[CH3:19])=[CH:5]/[CH2:6][CH2:7][C:8]([CH3:18])=[CH:9][CH2:10][CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.COC(C(=P(C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)C)=O>>[CH3:1][O:2][C:3](=[O:20])/[C:4](/[CH3:19])=[CH:5]/[CH2:6][CH2:7][C:8]([CH3:18])=[CH:9][CH2:10][CH2:11][C:12]1[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=1.[CH3:19]/[C:4](=[CH:5]\[CH2:6][CH2:7]/[C:8](/[CH3:18])=[CH:9]/[CH2:10][CH2:11][C:12]1[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=1)/[CH2:3][OH:2]

Participants

4

Reactant 2

HCID 10569721Methyl 2-(triphenyl-lambda~5~-phosphanylidene)propanoateHCID 68505655(E)-2,6-dimethyl-9-phenyl-2,6-nonadienoic acid methyl ester2×

Product 2

HCID 68505655(E)-2,6-dimethyl-9-phenyl-2,6-nonadienoic acid methyl esterHCID 68507693(2E,6E)-2,6-dimethyl-9-phenyl-2,6-nonadien-1-ol

Procedure

FIG. 24 depicts the preparation of (E)-9-phenyl-2,6-dimethyl-2,6-nonadienyl]-1-oxy-(tert.-butyl)dimethyl-silane (compound 43). In a coupling reaction hydrocinnamaldehyde (81) was converted to 2-methyl-5-phenyl-1-penten-3-ol (compound 82, CAS-No. 1836-38-0), from which (E)-4-methyl-7-phenyl-4-heptenoic acid ethyl ester (compound 83, CAS-No. 76620-37-6) was obtained. Reduction yielded (4E)-4-methyl-7-phenyl-4-heptenal (compound 84, CAS-No. 238736-71-5), which was transformed to (E)-2,6-dimethyl-9-phenyl-2,6-nonadienoic acid methyl ester (compound 85) in a Wittig-reaction using [1-(methoxycarbonyl)ethylidene]triphenylphosphorane (CAS-No. 2605-68-7). Reduction of compound (85) yielded (2E,6E)-2,6-dimethyl-9-phenyl-2,6-nonadien-1-ol (compound 86, CAS-No. 238736-72-6). Reaction with (tert.-butyl)dimethyl-silylchloride resulted in the formation of compound (43).

Sources & evidence

ORD record
ord-79a06342233d4afab361b70aaf70bd81
Source dataset
uspto-grants-2014_01
Patent number
US08629268B2

Reaction notes

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