Hydrochloric Acid → HCID 73117393, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of the silyl ether 186 (300 mg, 0.725 mmol) in THF (3 mL) at room temperature was added 1N aqueous solution of hydrochloric acid (3 mL). The mixture was stirred for 3 hours at 30° C. and then added a large volume of ethyl acetate and water. The water layer was washed with ethyl acetate and the combined organic layers were washed with brine, dried (MgSO4) and concentrated in vacuo. The crude residue was purified by flash chromatography (75% to 100% ethyl acetate/hexane) affording unsatisfactory purity. So the compound was purified again using 8% methanol in dichloromethane affording the title compound 187 in 33% yield (77 mg). 1H NMR: (300 MHz, CD3OD) δ: 7.87-7.71 (m, 4H), 7.52-7.40 (m, 3H), 6.77 (dt, J=15.1, 6.9 Hz, 1H), 5.75 (d, J=15.1 Hz, 1H), 4.76 (t, J=6.9 Hz, 1H), 2.17-2.10 (m, 2H), 1.84-1.77 (m, 2H), 1.49-1.27 (m, 4H) 1.88-1.75 (m, 4). MS (ESI)=282 (M+−OH), 322 (M++Na).

Provenance & Evidence