Pentane → HCID 22731317, compound

Participants

Reaction Steps

A stirred, cooled (−78° C.) solution of 5-bromo-3,3-dimethyl-2,3-dihydro-benzofuran (Intermediate 2, 1.44 g, 6.2 mmol) in 18 mL of anhydrous ether and 5 mL of anhydrous tetrahydrofuran under argon, was treated with a 1.7M solution of t-butyllithium in n-pentane (7.65 mL, 13.02 mmol) and the resulting solution was stirred at the same temperature for 1 h. Trimethyl borate (1.6 mL, 13.02 mmol) was added and the reaction mixture was allowed warm from −78° C. to −30° C. over 2 h. The reaction was quenched with saturated aqueous ammonium chloride solution and extracted with ether. The combined organic extract was dried over anhydrous sodium sulfate, filtered and evaporated to a foamy solid. Flash column chromatography using 25-100% ethyl acetate in hexane as the eluent afforded 0.57 g, 47.8% of the title compound as a white solid.

Provenance & Evidence