2-Chlorothiophene → (2S)-1-(5-chlorothiophen-2-yl)propan-2-ol

Participants

Reaction Conditions

Reaction Steps

A solution of 2-chlorothiophene (8.17 g) in tetrahydrofuran (80 ml) is cooled to -30° C. and 1.6M n-butyllithium in hexanes (43.0 ml) is added dropwise. The mixture is stirred at -30° C. for about 1 hour, (S)-propylene oxide (4.00 g) is added, and the mixture is warmed to 0° C. and stirred at that temperature for about 3 hours. The reaction is quenched with saturated aqueous ammonium chloride solution, diluted with ether, and the layers separated. The organic layer is washed with brine, dried over magnesium sulfate, and concentrated in vacuo to give the desired product.

Provenance & Evidence