3-(Methylsulfonyl)benzaldehyde → 1-(3-Methanesulfonylphenyl)ethan-1-ol

Participants

Reaction Conditions

Reaction Steps

Methylmagnesium iodide (3M in THF, 13.2 mL, 4.4 mmol) was added dropwise via syringe at 0° C. to 3-(methylsulfonyl)benzaldehyde (0.74 g, 4.0 mmol) in THF (15 mL). The resulting reaction mixture was stirred at 0° C. until no more conversion to product occurred (monitored by GC-MS). The reaction was quenched with saturated ammonium chloride, the aqueous phase was extracted with EtOAc and the organic phase was washed with saturated sodium bicarbonate, brine, dried (MgSO4), filtered and concentrated in vacuo. The crude product was purified by flash column chromatography on silica (EtOAc:hexane 1:4) to give the title compound (260 mg) that was used in the next step without any further purification (approximate purity 50%).

Provenance & Evidence