Triethylamine → 2-Azidoethyl methanesulfonate

Participants

Reaction Steps

To a solution of compound 2-azidoethanol (1.00 g, 11.49 mmol) in THF (25 mL) and triethylamine (Et3N) (2.418 mL, 17.24 mmol) was added mesyl chloride (1.328 mL, 17.24 mmol) at 0° C., and the mixture was allowed to warm to room temperature. Stirring continued for 3 h, during which TLC revealed a quantitative conversion into a higher Rf product. CH2Cl2 (70 mL) and saturated sodium bicarbonate (50 mL) were added, and the two layers were separated. The organic layer was washed with sodium bicarbonate (2×50 mL), saturated brine (45 mL) and dried over Na2SO4. Solvent was evaporated off to give crude compound 156a (1.70 g) as a colorless oil, which was used for next step without further purification.

Provenance & Evidence