Dimethyl Sulfoxide → HCID 15382135, compound

Participants

Reaction Conditions

Reaction Steps

A dry 100 mL round-bottom flask was charged with 15 mL of anhydrous CH2Cl2 and oxalyl chloride (2.8 mL, 2.0M in CH2Cl2, 5.6 mmol) and this solution was cooled to -78° C. A solution of DMSO (0.78 mL, 11.0 mmol) in 5 mL of CH2Cl2 was added dropwise and the resulting solution was stirred for 3 min. To this mixture, a solution of the alcohol 4 (1.92 g, 3.65 mmol) in 30 mL of CH2Cl2 was added dropwise and stirring was continued for 15 min. Triethylamine (1.5 mL, 11.0 mmol) was then introduced dropwise and the mixture was allowed to warm to room temperature over 15 min. The reaction mixture was poured into 50 mL of water, the layers were separated and the aqueous layer was extracted with 50 mL of CH2Cl2. The combined organic extracts were washed with water and brine, and dried over anhydrous MgSO4. Filtration, solvent removal and chromatography of the crude on silica gel afforded the ketone 5 (1.9 g, 99% yield) as pale yellow oil: Rf 0.7 (60% EtOAc/hexane); 13C-NMR (CDCl3) δ217.04, 173.21, 135.59, 132.99, 129.83, 129.77, 127.75, 127.72, 83.48, 71.34, 67.34, 65.79, 47.87, 34.61, 29.23, 28.83, 28.29, 26.89, 26.75, 24.90, 21.84, 19.19.

Provenance & Evidence