Dichloromethane → HCID 59779150, compound

Participants

Reaction Steps

BMS (8.10 mL, 107 mmol) was added to (1R)-1-(1-naphthyl)-3-oxabicyclo[3.1.0]hexan-2-one (12 g, 53.5 mmol) in dry tetrahydrofuran (100 mL) under nitrogen atmosphere. The reaction mass was refluxed for 5 hours and monitored by TLC (dichloromethane (100%)). The reaction was quenched with 10% potassium carbonate solution. The aqueous layer was extracted with dichloromethane (2×150 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): 0.87 (1H,m), 1.01-1.25 (2H,m,), 1.78-1.83 (2H,m,) 3.4-3.7 (2H,m), 4.12-4.18 (2H,m), 7.36-7.52 (4H,m), 7.57-7.75 (1H,m) 7.83-7.86 (1H,m) 8.25 (1H,brs).

Provenance & Evidence