Dimethyl Sulfoxide → HCID 18349299, compound

Participants

Reaction Conditions

Reaction Steps

1.02 g of oxalyl chloride were dissolved in 37 ml of CH2Cl2 and treated with 0.86 ml of dimethyl sulfoxide at −60° C. After shortly warming to −35° C., the reaction mixture was recooled to −60° C. and treated with a solution of 1.2 g of (1RS,2SR)-[2-(3,5-di-tert.butyl-2-ethoxy-phenyl)-cyclopropyl]-methanol in 20 ml of CH2Cl2. After 15 minutes of stirring at −50° C., 1.7 ml of triethylamine were dropped in. The reaction mixture was stirred for 2 hours at room temperature, poured on icewater, extracted with ether, washed (H2O), dried (Na2SO4) and evaporated. The crude material was purified by flash chromatography (silica gel, hexane:ethyl acetate=9:1) and recrystallized from hexane to give 1.01 g of (1RS,2RS)-2-(3,5- di-tert.butyl-2-ethoxy-phenyl)-cyclopropanecarbaldehyde as white crystals, m.p. 96-97° C.

Provenance & Evidence