Benzenepropanal → HCID 86645231, compound

HRID 1516973Notes

Reaction equation

HRID 1516973 reaction equation
C(=O)CCC1C=CC=CC=1.CC(C(O)CCC1C=CC=CC=1)=C.C([O:26][C:27](=O)[CH2:28][CH2:29]/[C:30](/[CH3:40])=[CH:31]/[CH2:32][CH2:33][C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1)C>>[CH3:40]/[C:30](=[CH:31]\[CH2:32][CH2:33][C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1)/[CH2:29][CH2:28][CH:27]=[O:26]

Participants

4

Reactant 3

HCID 7707BenzenepropanalHCID 11789744HCID 11789744, compound2×HCID 12697586HCID 12697586, compound2×

Product 1

HCID 86645231HCID 86645231, compound

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).

Workup

  1. customwas obtained

Sources & evidence

ORD record
ord-40af5cda5f9948e3bd2e6810c127e7e7
Source dataset
uspto-grants-2012_07
Patent number
US08227645B2

Reaction notes

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