Acrolein → HCID 57840754, compound

HRID 733426Notes

Reaction equation

HRID 733426 reaction equation
Br[C:2]([C:4]1[CH:9]=[CH:8][C:7]([O:10][CH3:11])=[C:6]([O:12][CH2:13][CH3:14])[CH:5]=1)=[CH2:3].[Li]C(C)(C)C.[CH:20]([CH:22]=[CH2:23])=[O:21]>>[CH2:13]([O:12][C:6]1[CH:5]=[C:4]([C:2]([CH:20]([OH:21])[CH:22]=[CH2:23])=[CH2:3])[CH:9]=[CH:8][C:7]=1[O:10][CH3:11])[CH3:14]

Participants

4

Reactant 3

HCID 7847AcroleinHCID 16085805HCID 16085805, compoundHCID 178418306HCID 178418306, compound

Product 1

HCID 57840754HCID 57840754, compoundYield 86.2%

Procedure

According to the General Procedure C, 1-bromo-1-(3-ethoxy-4-methoxyphenyl)ethene (1.40 g, 5.44 mmol), t-BuLi (8.00 ml, 13.60 mmol) and acrolein (914 mg, 16.32 mmol) are converted to give after workup and chromatography [SiO2, PE/EE gradient from 5:1 to 2:1, Rf (PE/EE=2:1)=0.31] the title compound (1.10 g, 4.69 mmol) as a colorless oil;

Sources & evidence

ORD record
ord-d9843dbfd2054f74b93f6f34e47dce2a
Source dataset
uspto-grants-2009_09
Patent number
US07589205B2

Reaction notes

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