4-Methylphenyl-2-propenal → 3-(4-Methylphenyl)but-3-en-2-ol
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]=1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
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.