Hydrochloric Acid → HCID 67433587, compound

Participants

Reaction Steps

Compound 4 (450 mg, 1.3 mmol) was dissolved in MeOH and treated with 3 N HCl at refluxed temperature for 3.5 h. After neutralized with solid NaHCO3, the solvent was removed and the residue was purified by vacuum silica gel column chromatography (MeOH:CH2Cl2=1:30 to 1:10) to give triol 5 (280 mg, 85%) as a white solid. mp 122-124° C.; [α]24D −123.05° (c 0.37, MeOH); 1H NMR (500 MHz, CD3OD) δ 7.46-7.30 (m, 5H), 5.34 (dd, J=1.0 and 3.0 Hz, 1H), 5.21 (s, 1H), 4.77 (d, J=12.0 Hz, 1H), 4.62 (d, J=12.5 Hz, 1H), 4.17-4.14 (m, 2H), 3.95-3.93 (m, 1H), 3.82-3.73 (m, 2H), 2.69-2.66 (m, 1H); 13C NMR (125 MHz, CD3OD) δ 148.9, 138.3, 128.0, 127.6, 127.3, 109.1, 80.8, 71.7, 71.0, 70.8, 61.8, 49.6; HR-MS Calcd. for (C14H18O4+H)+251.1283, found 251.1281.

Provenance & Evidence