Dimethyl Sulfoxide → 6-(2,6-Diethyl-phenyl)-4-ethoxy-pyridine-3-carbaldehyde

Participants

Reaction Conditions

Reaction Steps

A solution of dry DMSO (2.5 g, 32 mmol) in CH2Cl2 (2 mL) is added dropwise to a solution of oxalyl chloride (2M in CH2Cl2, 7.5 mL) in CH2Cl2 (80 mL) at −78° C. After 10 minutes, a solution of [6-(2,6-diethyl-phenyl)-4-ethoxy-pyridin-3-yl]-methanol (3.4 g, 11.4 mmol) in THF (20 mL) is added to the above mixture. Fifteen minutes after addition, TEA (10 mL) is added and the mixture is stirred at −78° C. for 15 minutes and then warmed to room temperature. The mixture is diluted with ether (100 mL) and washed with water (2×50 mL). The organic layer is dried and concentrated. The crude product is purified on a silica gel:column (4:1 Hexane/EtOAc) to give 6-(2,6-diethyl-phenyl)-4-ethoxy-pyridine-3-carbaldehyde. 1H NMR (CDCl3) 10.53 (s, 1H), 8.98 (s, 1H), 7.30 (t, 1H), 7.15 (d, 2H), 6.89 (s, 1H), 4.20 (q, 2H), 2.34 (m, 4H), 1.54 (t, 3H), 1.06 (t, 9H).

Provenance & Evidence