Hydrochloric Acid → HCID 10285953, compound
Reaction equation
[OH:1][C:2]1[CH:3]=[CH:4][C:5]2[O:9][C:8]([C:10]3[CH:18]=[CH:17][C:13]([C:14](O)=[O:15])=[CH:12][CH:11]=3)=[CH:7][C:6]=2[CH:19]=1.Cl>C1COCC1>[OH:15][CH2:14][C:13]1[CH:12]=[CH:11][C:10]([C:8]2[O:9][C:5]3[CH:4]=[CH:3][C:2]([OH:1])=[CH:19][C:6]=3[CH:7]=2)=[CH:18][CH:17]=1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
To a solution of 128 (0.15 g, 0.6 mmol), in THF (20 ml) was added BH3 (3 ml of 1.0 M in THF) and the reaction was heated to reflux for 3 hr. The reaction was then cooled and poured into 2N HCl and extracted with EtOAc. The EtOAc was dried over MgSO4, filtered and concentrated and triturated with CH2Cl2 and filtered to give 129 as a solid (0.08 g, 57%); 1H NMR (DMSO-d6) δ 9.21 (br s, 1 H), 7.82 (d, 2 H, J=8.1 Hz), 7.43–7.38 (m, 3 H), 7.24 (s, 1 H), 6.92 (d, 1 H, J=2.1 Hz), 6.73 (dd, 1 H, J=8.5 Hz, 2.6 Hz), 5.28 (t, 1 H, J=5.7 Hz), 4.54 (d, 2 H, J=5.5 Hz); MS 239 (M−H)−.