(Dimethyl sulfide)trihydroboron → (4-((1,3-Dioxolan-2-yl)methyl)phenyl)methanol

Participants

Reaction Conditions

Reaction Steps

To a cooled (0° C.) solution of 4-((1,3-dioxolan-2-yl)methyl)benzoic acid (1.02 g, 4.92 mmol) in anhydrous THF (63.5 mL), a solution of borane dimethylsulfide complex (2.0 M in THF, 12.29 mL, 24.59 mmol) was added dropwise. The reaction mixture was stirred at this temperature for 5 minutes and then the coolant removed. The reaction mixture was stirred at RT for 16 hours. The reaction mixture was cooled to 0° C. and methanol (1 mL) was added. The reaction mixture was diluted with water and saturated aqueous sodium hydrogen carbonate and then extracted with ethyl acetate (×2). The combined organic extracts were washed with brine, dried (magnesium sulphate) filtered, and concentrated under reduced pressure. The crude material was purified by silica gel chromatography eluting with 0-50% ethyl acetate in iso-hexane to afford the title compound (0.936 g, 98%).

Provenance & Evidence