Diethyl Ether → 2-(4-(Benzyloxy)phenyl)-2-(2-fluorophenyl)acetaldehyde

Participants

Reaction Steps

Dess-Martin periodinane (5.38 g, 12.7 mmol) was suspended in CH2Cl2 (70 mL). Compound 3 (3.22 g, 10.0 mmol) dissolved in 20 mL CH2Cl2, was added under stirring. The resulting mixture was stirred overnight at room temperature. Diethyl ether (200 mL) was added and the organic phase was washed with NaOH (2×30 mL, 2M), NaHCO3 (50 mL, saturated aqueous solution), and brine (50 mL) and dried over Na2SO4. Filtration and evaporation of the solvent under reduced pressure gave a crude material which was purified by column chromatography (heptane:ethyl acetate 4:1) to yield 2.76 g, 86% of 4 as a white solid. 1H-NMR (CDCl3) δ; 9.94 (dd, 1H, J=2.0 Hz and 1.5 Hz), 7.45-7.26 (m, 6H), 7.16 (d, 2H, J=8.6 Hz), 7.14-7.08 (m, 3H), 7.0 (d, 2H, J=9.0 Hz), 5.11 (ad, 1H, J=1.2 Hz), 5.07 (s, 2H); 13C-NMR (CDCl3) δ 197.6 (d, J=1.5 Hz), 160.7 (d, J=247 Hz), 158.5, 136.8, 130.5 (d, J=2.0 Hz), 130.5 (d, J=2.0 Hz), 129.3 (d, J=8.1 Hz), 128.6, 128.0, 127.4, 127.1, 124.4 (d, J=3.5 Hz), 115.7 (d, J=22.3 Hz), 115.5 (2C), 70.1, 57.1.

Provenance & Evidence