反应详情

温度

-78 °C

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).

1. additionis added
2. temperaturewarmed to room temperature
3. washwashed with water (2×50 mL)
4. customThe organic layer is dried
5. concentrationconcentrated
6. customThe crude product is purified on a silica gel