Diethyl chlorophosphate → HCID 88432937, compound

Participants

Reaction Steps

To a solution of 2--methylpropylphosphonic acid, dimethyl ester (2.20 g, 14.47 mmol) in anhydrous THF (200 ml) is added sec-butyllithium (20.04 ml, 26.05 mmol, 1.3M in cyclohexane) at 0° C. Following the addition, stirring is continued for an additional 30 minutes. This solution is then slowly added to a solution of diethyl chlorophosphate (2.50 9, 14.47 mmol) in anhydrous THF (100 ml) at room temperature. After stirring the reaction overnight, the mixture is quenched by the addition of a saturated aqueous solution of sodium bicarbonate and then extracted with methylene chloride. The combined organic extracts are dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure. The crude product is purified by flash chromatography with 30% acetone in hexanes on silica gel.

Provenance & Evidence