Sodium Iodide → (S)-1-(Benzyloxy)-2-[(diisopropylphosphono)methoxy]-3-iodopropane

Participants

Reaction Steps

A mixture of (R)-3-O-benzyl-2-O-[(diisopropylphosphono)methyl]-1-O-(methanesulfonyl)glycerol (10.0 g, 22.8 mmol) and sodium iodide (5.15 g, 34.4 mmol) in 70 mL of acetone was heated at reflux for 14 hours. The mixture was concentrated to about 30 mL volume, and insoluble material was removed by filtration. The filtrate was concentrated in vacuo, and the residue was purified by flash chromatography on silica gel (methylene chloride:acetone=1:0 to 5:1) to give 9.51 g (89%) of the title compound as an oil.

Provenance & Evidence