Benzaldehyde → 1-Phenylbut-3-en-1-ol

Participants

Reaction Steps

2.29 ml of a 1.4-molar solution of n-butyllithium (3.20 mmol) in pentane were added dropwise at 0° C. under argon for 2 minutes to a stirred solution of 500 mg (3.20 mmol) 2-methyl-3-isopropyl-hex-5-en-3-ol in 2 ml THF. The solution obtained was heated to room temperature, stirred for 15 minutes, and then a solution of 721 mg (3.20 mmol) ZnBr2 in 2 ml THF and subsequently 330 μl (3.20 mmol) benzaldehyde and 6 ml HMPA were added. The reaction mixture was heated to 70° C. and stirred for 6 hours at this temperature. Subsequently, it was cooled to room temperature and processed analogous to Example 1. 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