Dimethyl Sulfoxide → HCID 19002303, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of oxalyl chloride (371 μL, 548 mg, 4.32 mmol, 2 equivalents) in anhydrous CH2Cl2 (8 mL) at -78° C. under argon was added anhydrous DMSO (612 μL, 674 mg, 8.64 mmol, 4 equivalents) in anhydrous CH2Cl2 (8 mL) dropwise over 17 minutes. To the resulting clear, colorless solution was added 40 (961 mg, 2.16 mmol) in anhydrous CH2Cl2 (8 mL) dropwise at -78° C. over 15 minutes. The reaction was stirred at -78° C. (45 minutes) then NEt3 (3.00 mL, 2.18 g, 21.6 mmol, 10 equivalents) in anhydrous CH2Cl2 (8 mL) was added dropwise at -78° C. over 10 minutes. The resulting clear, light yellow solution was stirred at 0° C. (50 minutes), then shaken well with ice-cold 0.2 N HCl/brine (100 mL); extracted with EtOAc (3×75 mL); washed with ice-cold 0.2 N HCl/brine (2×50 mL); brine (2×100 mL); dried (MgSO4) and rotovapped (20° C.) once from CHCl3, then twice from CH2Cl2 and placed under high vacuum, yielding 41 as an oil (962 mg, 100%).

Provenance & Evidence