Acetone → HCID 86751718, compound

Participants

Reaction Conditions

Reaction Steps

(S)-2-O-(Diisopropyl phosphonomethyl)-3-butene-1,2-diol (2.62 g, 9.84 mmol) was mixed with triethylamine (1.99 g, 19.68 mmol) and 4-dimethylaminopyridine (10 mg) in 30 mL of methylene chloride. To the solution, mesyl chloride (1.35 g, 11.81 mmol) was slowly added at 0° C. The mixture was stirred at 0° C. for 30 min, then at room temperature for additional 30 min. Saturated sodium bicarbonate (50 mL) and methylen chloride (50 mL) were added. The aqueous layer was extracted with methylene chloride (75 mL×2). The combined methylene chloride extracts were dried over magnesium sulfate. The solvent was evaporated, and the residue was purified by flash chromatography (ethyl acetate:petroleum ether=1:1 to 1:0, then ethyl acetate:acetone=5:0 to 5:1) to provide 3.27 g (97% yield) of the title compound as an oil.

Provenance & Evidence