Ethanol → HCID 11781486, compound

Participants

Reaction Steps

To a solution of 24c (0.17 g 0.71 mmol) in dry ethyl ether (3 ml) was added dropwise a solution of phosphorus tribromide (μL 33.5, 0.36 mmol) in dry ethyl ether (0.7 ml); the reaction mixture was refluxed for 2 hours under argon atmosphere. After cooling to room temperature dry ethanol (μL 143) was added and the resulting solution was heated at reflux for 1 hour. Then 4 ml of aqueous sodium carbonate was added; the organic phase was separated, dried and evaporated. The crude product was chromatographed (50% petroleum ether 40-60° in dichloromethane) to give 0.103 g of pure 25c (48% yield). 1H NMR (CDCl3) δ7.35-7.16 (m, 2H); 6.92-6.82 (m, 2H); 6.39-6.37 (m, 1H); 6.13-6.09 (m, 1H); 5.69-5.64 (m, 1H); 5.10-5.01 (dd, 1H, J=14.57, 2.65 Hz); 4.70-4.59 (dd, 1H, J=14.88, 7.05 Hz).

Provenance & Evidence