Ethylene Oxide → 2-(6-methoxynaphthalen-2-yl)ethanol

Participants

Reaction Steps

tert-Butyllithium (5.2 mL, 8.84 mmol, 1.7 M/pentane) was added to a −78° C. solution of 2-bromo-6-methoxynaphthalene (1.0471 g, 4.42 mmol) in THF (10 mL)/ether (10 mL). After 30 minutes, a solution of ethylene oxide in THF (2 mL, 23 mmol, 0.5 g/mL) was added and the reaction was allowed to warm to room temperature. After overnight stirring, 30 mL saturated NH4Cl solution was added and the resulting mixture was extracted with ethyl acetate (3×30 mL). The combined organic solution was then dried (Na2SO4), filtered and evaporated. Purification by flash chromatography (ethyl acetate/hexanes) gave the title compound (478 mg, 53%).

Provenance & Evidence