Ethyl (diethoxyphosphoryl)methanesulfonate → HCID 86632005, compound

Participants

Reaction Conditions

Reaction Steps

A 2.5M solution of n-butyllithium in hexanes (6.15 mL, 15.37 mmol) was added dropwise to a stirred solution of (diethoxy-phosphoryl)-methanesulfonic acid ethyl ester (4.0 g, 15.37 mmol) in THF (200 mL) at −78° C. The reaction mixture was stirred at −78° C. for 15 minutes. A solution of 4-chloro-2-methoxy-benzaldehyde (2.41 g, 14.10 mmol) in THF (20 mL) was then added dropwise. After the addition was complete the reaction mixture was warmed to RT, stirred for 1 h and quenched with brine. The reaction mixture was concentrated under reduced pressure and DCM (200 mL) was added. The organic layer was separated, washed with brine (3×100 mL) and dried over MgSO4. Removal of solvent under reduced pressure, followed by purification on silica gel using hexane/ethyl acetate, 4:1 to 2:1 afforded the title compound (3.90 g, quantitative) as a white solid.

Provenance & Evidence