Dimethyl methylphosphonate → HCID 20082137, compound

Participants

Reaction Steps

To a solution of dimethyl methylphosphonate (6.6 ml, 60.5 mmol) in 100 ml of anhydrous THF was added dropwise n-butyl lithium (1.59N, 38.1 ml, 60.5 mmol) at -78° C. under argon atmosphere, and the mixture was stirred for 30 minutes. Then, methyl 3-cyclohexyl-2,2-dimethylpropionate (5.00 g, 25.2 mmol) was added dropwise and the mixture was stirred at -78° C. for 20 minutes and then at room temperature for 2 hours. An aqueous saturated solution of ammonium chloride was added to the reaction mixture. The mixture was extracted with ethyl acetate (50 ml×4) and then the combined ethyl acetate layers were washed with water (50 ml) and brine (50 ml), dried over anhydrous sodium sulfate, and concentrated. The residue was purified by column chromatography (silica gel, ethyl acetate) to yield a pure product of dimethyl 4-cyclohexyl-3,3-dimethyl-2-oxobutylphosphonate (3.9491 g, 13.6 mmol, 54.0%). This compound was assigned the structure by the following data:

Provenance & Evidence