Water → HCID 54532647, compound

Participants

Reaction Steps

1.84 g (4.99 mmol.) of (R)-3-t-butyldimethylsilyloxy-6-dimethoxyphosphinyl-5-oxohexanoic acid was dissolved in 11.5 ml of acetone. To the acetone solution were added 2.56 g (15.0 mmol.) of benzyl bromide and 0.76 g (5.5 mmol,) of potassium carbonate, and the resulting mixture was vigorously stirred for 6 hours at room temperature to give a reaction solution. The reaction solution was mixed with 12 ml of water and then extracted with 12 ml of toluene. The toluene portion was dried over anhydrous magnesium sulfate and concentrated to give an oil. The oil was treated by column chromatography (eluent: ethyl acetate) to give 1.99 g (4.34 mmol.) of benzyl (R)-3-t-butyldimethylsilyloxy-6-dimethoxyphosphinyl-5-oxohexanoate (optical purity: 99% ee) as an oil (yield: 87%).

Provenance & Evidence