Benzaldehyde → 1-Phenylbut-3-en-1-ol

Participants

Reaction Steps

1.94 ml of a 1.4-molar solution of n-butyllithium (2.71 mmol) in pentane were added dropwise at 0° C. under argon for 2 min to a stirred solution of 500 mg (2.71 mmol) 3-tert-butyl-2,2-dimethylhex-5-en-3-ol in 4 ml THF. The solution obtained was stirred for 15 minutes, and then a solution of 610 mg (2.71 mmol) ZnBr2 in 2 ml THF and subsequently 275 μl (2.71 mmol) benzaldehyde were added. The reaction mixture was stirred for 1 hour and heated to room temperature. Subsequently, 15 ml NH4Cl solution were added. The organic components were extracted three times with 15 ml Et2O each, the combined organic phases were washed with 10 ml brine, then dried and concentrated under reduced pressure. The raw product obtained was cleaned by means of a silica column with 15% diethyl ether/light gasoline. There was obtained the alcohol as a colorless oil.

Provenance & Evidence