Water → HCID 10125597, compound

Participants

Reaction Conditions

Reaction Steps

To a mixture of 2,8-dimethoxy-12-propyl-6H-dibenzo[c,h]chromene (220 mg, 0.658 mmoles) in CH2Cl2 (33 ml) at 0° C. was slowly added boron tribromide (3.95 ml of 1 N solution in CH2Cl2, 3.95 mmols). The reaction mixture was stirred at 0° C. for 3 h. 4 ml water was injected into the mixture with stirring in an ice-water bath. CH2Cl2 in the mixture was removed under reduced pressure. The resulting mixture was extracted with ethyl acetate (x3). The combined organic layers were washed with brine, dried over sodium sulfate, filtered, and stripped of solvent to give 120 mg (60%) of the title compound as white solid. The analytical sample was obtained by purification with silica column chromatography (20%-30% ethyl acetate—hexane) and then recrystalliazation with ethyl acetate—hexane: mp 86-95° C.; 1H NMR (DMSO-d6): δ 1.00 (3H, t, J=7.24 Hz), 1.63-1.76 (2H, m), 2.87 (2H, t, J=7.22 Hz), 5.16 (2H, s), 6.69 (1H, d, J=2.28 Hz), 6.79 (1H, dd, J=8.39 Hz, J=2.28 Hz), 7.03 (1H, dd, J=9.02 Hz, J=2.18 Hz), 7.20 (1H, d, J=2.10 Hz), 7.60 (1H, s), 7.62 (1H, d, J=7.85 Hz), 7.99 (1H, d, J=9.01 Hz), 9.61 (1H, s), 7.76 (1H, s); MS (ESI) m/z 305 (M−H)−, 307 (M+H)+; HRMS: calcd for C20H18O3, 306.1256; found (ESI),305.11827.

Provenance & Evidence