Dimethyl Sulfoxide → Di(tert-butyl) (4-methylbenzoyl)phosphonate

Participants

Reaction Conditions

Reaction Steps

To a solution of oxalyl chloride (1.75 mL) in CH2Cl2 (60 mL) cooled at −78° C. was added DMSO (2.8 mL) dropwise. The mixture was stirred for 10 min at −78° C. and a solution of di(tert-butyl) hydroxy(4-methylphenyl)methylphosphonate (3.14 g in 20 mL of CH2Cl2 was introduced dropwise. After stirring for 30 min at −78° C., 14 mL of Et3N was added. The resulting mixture was stirred for 30 min at −78° C. and 45 min at room temperature, and then quenched with 200 mL of 50% saturated aqueous NaCl solution. The mixture was extracted with 2×200 mL of 1:1 hexane/EtOAc and the extract was dried over MgSO4 and concentrated to give 3 g of the title compound as a yellow oil.

Provenance & Evidence