Dimethyl Sulfoxide → HCID 59815097, compound

Participants

Reaction Conditions

Reaction Steps

A solution of DMSO (120 μL, 1.69 mmol) in 1 mL CH2Cl2 was added to a −78° C. solution of oxalyl chloride in CH2Cl2 (400 μL, 0.80 mmol, 2 M), rinsing with 1 mL CH2Cl2. The reaction was stirred at −78° C. for 30 min. and then a solution of 5 (297 mg, 0.49 mmol) in 1.2 mL CH2Cl2 was added dropwise by cannula, rinsing with 1.2 mL. Et3N (400 μL, 2.9 mmol) was added and the reaction was allowed to warm to room temperature. After 5 h, 60 mL H2O was added and the resulting mixture was extracted with CH2Cl2 (3×50 mL). The combined CH2Cl2 solution was washed with brine and then was dried (Na2SO4), filtered and evaporated. The residue was purified by flash chromatography on silica gel (0%→100% ethyl acetate/hexanes) to give compound 6 (276 mg, 99%).

Provenance & Evidence