Dichloromethane → 6-(Dimethoxythiophosphoryl)hexanoic acid tert-butyl ester

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Reaction Steps

A solution of dimethylthiophosphite (4.56 g, 36.2 mmol), 6-bromohexanoic acid tert-butyl ester (100 g, 39.8 mmol) and triethylbenzylammonium chloride (0.82 g, 3.62 mmol) in dichloromethane (100 mL) was cooled on an ice bath and a solution of sodium hydroxide (14.5 g, 0.362 mol) in water (14.5 mL) was added slowly with vigorous stirring. The ice bath was removed and the mixture stirred for 3 days before being washed with water, dried (magnesium sulfate), and the solvent removed under reduced pressure to give crude 6-(dimethoxythiophosphoryl)hexanoic acid tert-butyl ester (8.00 g).

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