Tetrahydrofuran → Diphenyl chlorophosphate

Participants

Reaction Conditions

Reaction Steps

Compound 6 (0.75 g) is first dissolved in refluxing dioxane, evaporated to dryness under reduced pressure, and then dissolved in 600 mL THF. The solution is cooled to -78° C. To this solution is slowly added 4.8 mL (2 eq) butyllithium solution, and the resultant cloudy mixture is stirred at 78° C. for 1 hour. A solution of 2.61 g (2.6 eq) diethyl chlorophosphate in 10 mL THF is then added dropwise. The mixture is maintained at -78° C. for three hours and then quenched by the dropwise addition of 10 mL distilled water, at which point the product precipitated from solution. The mixture is warmed to room temperature and filtered to give a white solid. The product is washed with distilled water, hot THF, toluene, ethanol, and DMF and dried under vacuum. Yield: 0.2 g. IR (cm-1): 3300-3150, 2966, 1601, 1492, 1389, 1280, 1216, 1120, 1030, 934, 844, 767.

Provenance & Evidence