Ammonia → 2-(1-Adamantyl)ethyl p-toluene-sulfonate

Participants

Reaction Steps

To a solution of 1-adamantaneethanol (3.06 g, 16.9 mmol) and triethylamine (2.8 mL, 20.1 mmol) in methylen chloride (30 mL) was added at 0° C. a suspension of 4-methylbenzene-1-sulfonyl chloride (3.88 g, 20.3 mmol) in methylen chloride (40 mL). The reaction mixture was stirred at room temperature overnight. Then, ice and a solution of ammonia 50% in water were added into the reaction mixture. The mixture was extracted with pentane and the organic layer was washed with water and brine. The solvent was removed under reduced pressure and the title compound was obtained as an oil (5.4 g, 90%). MS (M+): 335.

Provenance & Evidence