Tetrahydrofuran → HCID 22356917, Verbindung

Reaktionsgleichung

[CH3:1][C:2]([O:14][C:15]1[CH:16]=[C:17]2[C:21](=[CH:22][CH:23]=1)[CH2:20][CH:19]=[C:18]2[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)([C:4]1[CH:13]=[CH:12][C:7](C(OC)=O)=[CH:6][CH:5]=1)[CH3:3].[OH-:30].[Na+].[O:32]1[CH2:36]CCC1>CO>[CH3:3][C:2]([C:4]1[CH:5]=[CH:6][CH:7]=[CH:12][C:13]=1[C:36]([OH:32])=[O:30])([O:14][C:15]1[CH:16]=[C:17]2[C:21](=[CH:22][CH:23]=1)[CH2:20][CH:19]=[C:18]2[C:24]1[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=1)[CH3:1]

Komponenten

Versuchsvorschrift

Methyl 4-(1,1-dimethyl-3-phenyl-1H-inden-5-yloxymethyl)benzoate (300 mg, 0.78 mmol) and 3.9 mL of 2N NaOH in 5 mL of tetrahydrofuran and 5 mL of methanol were stirred at room temperature for 16 hours. The mixture was concentrated and acidified with 1N HCl (10 mL), extracted with ethyl acetate (20 mL×3). The combined extracts were washed with water (10 mL), dried over magnesium sulfate, and evaporated. The residue was crystallized from ether-hexane to give 247 mg (85% yield) of the title compound as white crystals; 1H-NMR (DMSO-d6) δ 1.31 (s, 6H), 5.20 (s, 2H), 6.57 (s, 1H), 6.89 (dd, J=1.1, 8.2 Hz, 1H), 7.02 (d, J=1.1 Hz, 1H), 7.36-7.57 (m, 8H), 7.95 (d, J=8.3 Hz, 2H), 12.94 (bs, 1H); MS m/e 371 (MH+).