Propyltriphenylphosphonium bromide → Methyl 3-(hex-3-en-1-yl)-4,5-dimethoxybenzoate

HRID 638919Notes

Reaction equation

[CH3:1][O:2][C:3](=[O:18])[C:4]1[CH:9]=[C:8]([CH2:10][CH2:11][CH:12]=O)[C:7]([O:14][CH3:15])=[C:6]([O:16][CH3:17])[CH:5]=1.[Br-].[CH2:20]([P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[CH2:21][CH3:22]>>[CH3:1][O:2][C:3](=[O:18])[C:4]1[CH:5]=[C:6]([O:16][CH3:17])[C:7]([O:14][CH3:15])=[C:8]([CH2:10][CH2:11][CH:12]=[CH:20][CH2:21][CH3:22])[CH:9]=1

Participants

Reactant 2

HCID 80374Propyltriphenylphosphonium bromide

HCID 71378647Methyl 3,4-dimethoxy-5-(3-oxopropyl)benzoate

Product 1

HCID 68684188Methyl 3-(hex-3-en-1-yl)-4,5-dimethoxybenzoate

Procedure

3-Hex-3-enyl-4,5-dimethoxybenzoic acid methyl ester was prepared from 3,4-dimethoxy-5-(3-oxopropyl)benzoic acid methyl ester and propyltriphenylphosphonium bromide by following Method J. The crude product was purified by flash column chromatography on silica gel using 20% EtOAc in hexanes as an eluent to furnish 3-hex-3-enyl-4,5-dimethoxybenzoic acid methyl ester in 63% yield.

Workup

customThe crude product was purified by flash column chromatography on silica gel using 20% EtOAc in hexanes as an eluent

Sources & evidence

ORD record: ord-de6157c2440949a1819bd617346d3dfe
Source dataset: uspto-grants-2010_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07691843B2

Reaction notes

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