Aluminum(III) Chloride → 2-(Hexan-2-YL)thiophene

Participants

Reaction Conditions

Reaction Steps

Under nitrogen, a suspension of LiAlH4 (4.9 g, 0.13 mol) in dry Et2O (700 mL) was cooled to 0° C. by an ice/water bath. AlCl3 (34.4 g, 0.26 mol) was then added in small portions. After addition, the mixture was stirred at 0° C. for 1 hour. A solution of 2-thiophen-2-yl-hexan-2-ol in dry Et2O (13.1 g, 70.81 mmol) was then added dropwise. The mixture was stirred at 0° C. for 2 hours, and allowed to warm to room temperature, and stirred at room temperature overnight. After cooling to 0° C., the reaction was quenched by adding water. The reaction mixture was washed with water and brine, dried over Na2SO4, and concentrated on a rotary evaporator. The residue was subjected to column chromatography on silica gel with hexane as the eluent, leading to a colorless oil as the product (6.0 g, 50.3%).

Provenance & Evidence