Dimethyl Sulfoxide → 2-[1-(2-Oxopropyl)cyclopropyl]acetonitrile

Participants

Reaction Steps

To a -78° C. solution of oxalyl chloride (0.70 mL, 8.0 mmol) in 40 mL of CH2Cl2 was added DMSO (0.62 mL, 8.7 mmol) and the resulting solution was stirred for 10 min. A solution of the alcohol from Step 3 (2.46 g, 17.7 mmol) in 5 mL CH2Cl2 was then added, and the mixture stirred 1 h at -78° C. Triethylamine (4.2 mL, 30 mmol) was then added, and the solution was allowed to warm to room temperature and stirred overnight. The reaction mixture was then partitioned between 1M HCl and CH2Cl2, and the organic layer was washed with saturated NaHCO3 and brine, dried over MgSO4 and evaporated. Purification of the residue by flash chromatography (25% ethyl acetate/hexanes) provided 927 mg of the title compound.

Provenance & Evidence