Acetic Acid → Dimethyl (2-oxo-3-(3-(trifluoromethyl)phenyl)propyl)-phosphonate

Participants

Reaction Steps

To a solution of dimethyl methylphosphonate (9.4 g, 75.8 mmol) in toluene (80 mL) at −78° C. was slowly added n-BuLi (2.5M in hexanes, 28 mL, 70 mmol). The reaction mixture was stirred for 1 h and a solution of N-methoxy-N-methyl-2-(3-trifluoromethyl-phenyl)-acetamide (14.39 g) in toluene (50 mL) was slowly added. The reaction mixture was stirred for 2.5 h and AcOH (40 mL) was added. The reaction mixture was warmed to room temperature and water was added. The organic layer was washed with water followed by brine. The organic solution was dried (MgSO4), filtered and concentrated in vacuo. Medium pressure chromatography (CH2Cl2 to 2% MeOH in CH2Cl2) provided the title compound of Preparation 3 (9.37 g). 1H NMR (CDCl3) δ7.52 (m, 1H), 7.44 (m, 2H), 7.37 (m, 1H), 3.96 (s, 2H), 3.87 (s, 3), 3.76 (s, 3H), 3.12 (d, 2H).

Provenance & Evidence