Acetic Acid → Dimethyl 3-(3-Methoxymethylphenyl)-2-oxopropylphosphonate

Participants

Reaction Steps

Under an atmosphere of argon gas, a solution of dimethyl methylphosphonate (DMMP; 147 g) in anhydrous toluene (1500 ml) was cooled to −74° C. Thereto, n-butyllithium (714 ml; 1.52 M in hexane) was added for 1 hour. The mixture was stirred for 1 hour. Thereto, a solution of N-methoxy-N-methyl-(3-methoxymethylphenyl)acetic acid amide (200 g; prepared in Reference Example 20) in anhydrous toluene (400 ml) was added for 30 minutes. In addition, the mixture was stirred for 2 hours. Thereto, acetic acid (73.5 ml) was added. The mixture was heated to room temperature and poured into water. The organic layer was separated. The organic layer was washed by water and an aqueous saturated solution of sodium chloride successively, dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was purified with silica gel column chromatography to obtain the title compound (206.5 g).

Provenance & Evidence