Acrolein → 3,4-Dimethoxyphenyl-1,4-pentadien-3-ol

Reaction equation

Br[C:2]([C:4]1[CH:9]=[CH:8][C:7]([O:10][CH3:11])=[C:6]([O:12][CH3:13])[CH:5]=1)=[CH2:3].[Li]C(C)(C)C.[CH:19]([CH:21]=[CH2:22])=[O:20]>>[CH3:13][O:12][C:6]1[CH:5]=[C:4]([CH:2]=[CH:3][CH:19]([OH:20])[CH:21]=[CH2:22])[CH:9]=[CH:8][C:7]=1[O:10][CH3:11]

Participants

Reactant 3

HCID 7847Acrolein

HCID 160853611-Bromo-1-(3,4-dimethoxyphenyl)ethene

HCID 178418306HCID 178418306, compound

Product 1

HCID 867612173,4-Dimethoxyphenyl-1,4-pentadien-3-olYield 42.3%

Procedure

According to the General Procedure C, 1-Bromo-1-(3,4-dimethoxyphenyl)ethene (1.00 g, 4.11 mmol), t-BuLi (6.05 ml, 10.28 mmol) and acrolein (691 mg, 12.33 mmol) are converted to give after workup and chromatography (SiO2, PE/EE=2:1, Rf=0.25) the title compound (382 mg, 1.74 mmol, 42%) as a yellow oil; C13H16O3 (220.26).

Sources & evidence

ORD record: ord-4c9d4465d7f047c0abcc3e3ab3775dac
Source dataset: uspto-grants-2010_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07838521B2

Reaction notes

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