Acetic Acid → Dimethyl 2-oxo-3-phenoxypropylphosphonate

Participants

Reaction Conditions

Reaction Steps

n-Butyl lithium (69 ml. of a 1.2 M solution in hexane) was added to a solution of dimethyl methylphosphonate (10.3 g.) in dry tetrahydrofuran at -78° C. in an atmosphere of nitrogen. After 10 minutes, a solution of phenoxyacetylchloride (4.1 g.) in dry tetrahydrofuran (20 ml.) was added dropwise, and the mixture was stirred for 4 hours at -78° C. The reaction mixture was neutralised with acetic acid and the solvents were removed under reduced pressure. The residue was shaken with a mixture of ether (100 ml.) and water (20 ml.), and the organic phase was separated and washed with brine. The solution was dried, the solvents were evaporated and the residue was distilled in a bulb distillation apparatus at an oven temperature of 160° C. and 0.1 mm. pressure, to give dimethyl 2-oxo-3-phenoxypropylphosphonate.

Provenance & Evidence