4-Methylphenyl-2-propenal → 3-(4-Methylphenyl)but-3-en-2-ol

HRID 1359546Notes

Reaction equation

[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=[CH2:11])[CH:9]=[O:10])=[CH:4][CH:3]=1.[CH3:12][Li]>C(OCC)C>[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=[CH2:11])[CH:9]([OH:10])[CH3:12])=[CH:4][CH:3]=1

Participants

Conditions

Temperature: -78 °C

Procedure

2.34 g of aldehyde 38 is dissolved in 150 ml of diethyl ether and cooled to −78° C. under nitrogen. 20 ml of methyllithium solution (1.6 M in diethyl ether) is now added in drops. After 1.5 hours at this temperature, it is quenched with saturated ammonium chloride solution, extracted with ethyl acetate, washed with sodium chloride solution, dried on sodium sulfate, and the solvent is removed. The residue is purified by chromatography on silica gel with ethyl acetate/hexane, whereby in addition to 237 mg of starting material, 1.06 g of title compound 39 accumulates as a colorless oil.

Workup

customAfter 1.5 hours at this temperature, it is quenched with saturated ammonium chloride solution
extractionextracted with ethyl acetate
washwashed with sodium chloride solution
customdried on sodium sulfate
customthe solvent is removed
customThe residue is purified by chromatography on silica gel with ethyl acetate/hexane, whereby in addition to 237 mg of starting material, 1.06 g of title compound 39 accumulates as a colorless oil

Sources & evidence

ORD record: ord-e4564aa4001a43a6a3edb3af034ba5eb
Source dataset: uspto-grants-2003_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06600058B1

Reaction notes

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