Dimethyl Sulfoxide → 1-(((Tert-butyldimethylsilyl)oxy)methyl)cyclopropane-1-carbaldehyde

Participants

Reaction Conditions

Reaction Steps

To a stirred solution of DMSO (6.9 mL, 0.097 mol) in anhydrous DCM (90 mL) at −70° C. was added oxalyl chloride (4.20 mL, 0.0486 mol). After stirring for 10 min. at −70° C., a solution of [1-({[tert-butyl(dimethyl)silyl]oxy}methyl)cyclopropyl]methanol (7.011 g, 0.03240 mol) in anhydrous DCM (30 mL) was added via cannula. The resulting milky mixture was slowly warmed to −55° C. over 45 min. DIPEA (34.0 mL, 0.194 mol) was added. The resulting mixture was stirred for 5 min. at −55° C., and then the cooling bath was removed and the reaction mixture was allowed to warm to RT. The reaction was then quenched with saturated aqueous NaHCO3 (150 mL) and extracted with DCM (2×). The combined organic layers were washed with brine, dried over magnesium sulfate, filtered and concentrated in vacuo. The resulting residue was purified by Combiflash chromatography eluting with 0-10% EtOAc/hexanes to afford the desired product as a colorless oil (4.558 g, 66% yield).

Provenance & Evidence