Sulfuric Acid → Pyridin-2-yl(2-m-tolyltetrahydrofuran-2-yl)methanone

Participants

Reaction Conditions

Reaction Steps

To a solution of 2-bromopyridine (418 mg, 2.65 mmol) in THF (10 mL) was added n-BuLi (1.65 mL, 2.65 mmol, 1.6 N in hexane) at −78° C. After 15 mins, a solution of Example 91C (4.45 mg, 1.76 mmol) in THF (2 mL) was added. The mixture was stirred at −78° C. for 15 minutes and 2 mL of 1 M H2SO4 was added slowly. Then the mixture was heated at 50° C.-60° C. for 30 minutes. After cooling to room temperature, the aqueous phase was separated and extracted with ethyl acetate (15 mL×3). The combined organic phases was washed with water (50 mL) and brine (50 mL), dried over Na2SO4, filtered, and concentrated to provide the title compound. LC-MS: m/z (M+H): 268.

Provenance & Evidence