Dimethyl Sulfoxide → HCID 11731420, compound

Participants

Reaction Conditions

Reaction Steps

At −78° C. a solution of oxalyl chloride (200 μL, 2.34 mmol) in anhydrous DCM (20 mL) is treated with anhydrous DMSO (310 μL, 4.37 mmol). After 15 min of stirring at −78° C., a solution of Example 4 (1.0 g, 1.76 mmol) in anhydrous DCM (5 mL) is added dropwise. The resulting mixture is allowed to stir for 40 min at −78° C. and TEA (1250 μL) is added neat. After 10 min the reaction mixture is allowed to warm up to −30° C. After 1 hour of stirring at −30° C. the reaction mixture is quenched with water (50 mL). Extraction with DCM (3×100 mL), drying over MgSO4 and evaporation under reduced pressure gives a yellow oil. Flash chromatography on a 4×21 cm2 SiO2 column using Et2O/MeOH (100/1) mixture then (100/3) as eluant gives the title compound as a pale yellow foam (0.804 g, 1.42 mmol) in a 81% yield.

Provenance & Evidence