Pyridine → HCID 57794586, compound

Participants

Reaction Conditions

Reaction Steps

Glyoxylic acid monohydrate (4.0 g, 43.45 mmol) was suspended in diethyl phosphite (5.59 mL, 1.0 equiv), warmed to 60° C., and held there for 5 h. The reaction was cooled, diluted with dichloromethane (40 mL), and treated with pyridine (3.51 mL, 1.0 equiv) and acetyl chloride (3.09 mL, 1.0 equiv). A significant exotherm was noted. The reaction was stirred at room temperature for 2 h. The reaction was washed with 1M hydrochloric acid (2×20 mL), then saturated sodium bicarbonate. The organics were dried over magnesium sulfate, and concentrated to give <2 g as an oil. The aqueous washes were combined and extracted with dichloromethane (4×). The organics were dried over magnesium sulfate and concentrated to give 5.85 g (53%) as an oil which solidified upon standing. 1H-NMR (CDCl3, 500 MHz) δ 1.36 (t, J=7.0, 6H), 2.21 (s, 3H), 4.28 (m, 4H), 5.54 (d, J=17.7, 1H), 8.90 (bs, 1H). Mass spec.: 255.10 (MH)+.

Provenance & Evidence