(4-Methoxybenzyl)(triphenyl)phosphonium bromide → 1-Methoxy-4-[(5E)-undeca-1,5-dien-1-yl]benzene
Reaction equation
[Br-].[CH3:2][O:3][C:4]1[CH:9]=[CH:8][C:7]([CH2:10][P+](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=[CH:6][CH:5]=1.[CH:30](=O)[CH2:31][CH2:32]/[CH:33]=[CH:34]/[CH2:35][CH2:36][CH2:37][CH2:38][CH3:39]>C1COCC1>[CH3:2][O:3][C:4]1[CH:5]=[CH:6][C:7]([CH:10]=[CH:30][CH2:31][CH2:32]/[CH:33]=[CH:34]/[CH2:35][CH2:36][CH2:37][CH2:38][CH3:39])=[CH:8][CH:9]=1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
Starting from (4-methoxyphenyl)methyltriphenylphosphonium bromide (14.0 g, 30.2 mmol, 1.0 equiv.), KtBuO (34 mL, 34.0 mmol, 1.1 equiv., 1M in THF) and (E)-dec-4-enal (5.59 g, 36.3 mmol, 1.2 equiv.), 5.59 g (72%) of the title compound was obtained after purification by flash chromatography on SiO2 (cyclohexane/EtOAc 99:1) as a light yellow oil.