2,3-Dihydrofuran → (2-Bromo-3-methylphenyl)(4,5-dihydrofuran-2-yl)methanone

Participants

Reaction Conditions

Reaction Steps

A solution of 2,3-dihydrofuran (0.70 mL, 9.25 mmol) in THF (9.0 mL) under inert atmosphere was cooled to −78° C. A solution of n-butyllithium, 1.7 M in pentanes (5.98 mL, 10.17 mmol), was added dropwise over 10 min. The reaction was maintained at that temperature for 30 min, and allowed to warm to 0° C. for 30 min. It was cooled back down to −78° C. and then added via cannula to a solution of (2-bromo-3-methylphenyl)(morpholino)methanone (2.02 g, 7.12 mmol) in Et2O (17.92 mL), also at −78° C. The solution was stirred at that temperature for 10 min and then allowed to warm to 0° C. The mixture was partitioned between Et2O and water and the organics were washed with water and brine. The solution was dried over Na2SO4 and concentrated. The crude material was absorbed onto a plug of silica gel and purified by column chromatography eluting with a gradient of Et2O in hexane, to provide (2-bromo-3-methylphenyl)(4,5-dihydrofuran-2-yl)methanone as a colorless oil. This oil was immediately re-dissolved in Et2O and placed under nitrogen before storing in the freezer for further use.

Provenance & Evidence