Sodium borohydride → 2-(4-(Benzyloxy)tetrahydrofuran-2-yl)ethanol
反応式
[CH2:1]([O:8][CH:9]1[CH2:13][O:12][CH:11]([CH2:14][CH:15]=[O:16])[CH2:10]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[BH4-].[Na+]>CO>[CH2:1]([O:8][CH:9]1[CH2:13][O:12][CH:11]([CH2:14][CH2:15][OH:16])[CH2:10]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1参加物
4
実験手順
To a stirred solution of 2-(4-(benzyloxy)tetrahydrofuran-2-yl)acetaldehyde (2.46 g, 11.17 mmol) in methanol (50 mL) was added NaBH4 (0.423 g, 11.17 mmol), in small portions, at room temperature. After 2 h, the reaction mixture was concentrated and the residue was taken up in sat. Na2CO3 (25 mL) and extracted with CH2Cl2 (3×25 mL). The combined CH2Cl2 layers were dried (Na2SO4), filtered and concentrated to give 2-(4-(benzyloxy)tetrahydrofuran-2-yl)ethanol (2.3847 g, 10.73 mmol, 96% yield) as a colorless oil consisting of a ˜4:1 mixture of diastereomers. 1H NMR (500 MHz, CDCl3) δ: 7.23-7.38 (5 H, m), 4.49 (1.6 H, s), 4.42 (0.4 H, d, J=1.5 Hz), 4.17-4.29 (1 H, m), 3.99-4.11 (2 H, m), 3.74-3.82 (2 H, m), 3.70 (0.8 H, dd, J=9.8, 4.9 Hz), 3.61 (0.2 H, dd, J=9.9, 5.0 Hz), 2.52 (0.8 H, t, J=5.6 Hz), 2.48 (0.2 H, t, J=5.6 Hz), 2.30 (0.8 H, dt, J=13.6, 7.2 Hz), 2.16-2.25 (0.2 H, m), 1.61-1.99 (3 H, m). LCMS (M+H) calcd for C13H19O3: 223.13; found: 223.07.