Dimethyl methylphosphonate → HCID 87946522, compound

Participants

Reaction Steps

A solution of 0.46 mL of 2 M n-butyllithium in hexanes in 4 mL of THF at −78° C. was treated with 0.10 mL (0.92 mmol) dimethyl methylphosphonate and strirred cold for 50 min. (+/−)-2-Methyl-4-formyl-4-(2-(4-octylphenyl)ethyl)oxazoline (252 mg, 0.76 mmol, from EXAMPLE 2, Step B) was added and the resulting solution was stirred cold for 5 h. The mixture was treated with 0.32 mL (2.3 mmol) of phenyl chlorothionoformate and stirred cold for 1 h. The reaction was quenched with 2 mL of sat'd NH4Cl, then extracted with 30 mL of CH2Cl2. The organic layer was separated, washed with sat'd NaHCO3, dried and concentrated. Flash chromatography on silica gel using hexanes/EtOAc/CH3CN as the eluant afforded 75 mg (17%) of the title compound as a mixture of isomers: Mass spectrum (NH3—CI) 590 (M+H).

Provenance & Evidence