Dichloromethane → HCID 59779155, compound

Participants

Reaction Steps

BMS (17.16 mL, 18 mmol) was added to (1R)-1-(3,4-dichlorophenyl)-3-oxabicyclo[3.1.0]hexan-2-one (22 g, 9 mmol) in dry tetrahydrofuran (200 mL), under nitrogen atmosphere. The reaction mass was refluxed for 5 hours and monitored by TLC (dichloromethane (100%)). The reaction mass was quenched with 10% potassium carbonate solution. The aqueous layer was extracted with dichloromethane (2×250 mL). The combined organic layer was dried over anhydrous sodium sulfate, filtered and evaporated under reduced pressure to yield 20.4 g (92%) of desired product. 1H NMR δ(300 MHz,CDCl3): 0.9-1.25 (1H,m), 1.35-1.52 (1H,m), 1.75-1.79 (1H,m), 3.32-3.42 (2H,m) 3.97-4.12 (2H,m) 7.26-7.30 (1H,dd,J=8.4,2.1 Hz), 7.40-7.43 (1H,d,J=8.4 Hz), 7.52-7.53 (1H,d,J=2 Hz).

Provenance & Evidence