Hydrochloric Acid → 2-(4-(Benzyloxy)phenyl)-2-(2-fluorophenyl)ethanol

Participants

Reaction Conditions

Reaction Steps

Compound 2 (4.01 g, 13.1 mmol) was dissolved in THF (30 mL) and the solution was cooled to 0° C. BH3·THF (26.3 mL, 26.3 mmol, 1.0 M) was added drop-wise and the mixture was allowed to stir at room temperature for 3 h. The mixture was cooled to 0° C. and 10% H2O in THF (8 mL), 5.6 g NaOH (dissolved in 30 mL H2O), and 46 g H2O2 (35%) were sequentially added. The mixture was stirred overnight at room temperature. The mixture was acidified with aqueous HCl and extracted with diethyl ether (3×50 mL). The organic phase was washed with NaHCO3 (50 mL, saturated aqueous solution), brine (50 mL), and dried over Na2SO4. Evaporation of the solvent gave 4.20 g as a crude oil. Column chromatography (heptane:ethyl acetate 4:1 to 2:1) gave 3.22 g, 76% as a semisolid. 1H-NMR (CDCl3) δ; 7.46-7.26 (m, 6H), 7.25-7.18 (m, 1H), 7.21 (d, 2H, J=8.6 Hz), 7.11 (ddd, 1H, J=8.0 Hz, J=7.4 Hz and J=1.4 Hz), 7.04 (ddd, 1H, J=10.6 Hz, J=8.2 Hz and J=1.4 Hz), 6.94 (d, 2H, 8.8 Hz), 5.04 (s, 2H), 4.49 (t, 1H, 7.0 Hz), 4.15 (d, 2H, J=7.2 Hz), 1.54 (s, H2O/OH); 13C-NMR (CDCl3) δ 161.0 (d, J=246 Hz), 157.8, 137.0, 132.6, 129.3, 128.9 (d, J=4.6 Hz), 128.8 (d, J=14.6 Hz), 128.6, 128.3, 127.9, 127.4, 124.2 (d, J=3.8 Hz), 115.7 (d, J=22.7 Hz), 115.1, 70.0, 54.2 (d, J=1.5 Hz), 45.8 (d, J=1.9 Hz).

Provenance & Evidence