Sodium hydride → HCID 58780780, compound

Participants

Reaction Conditions

Reaction Steps

To a suspension of sodium hydride (8.8 g, 0.220 mol) in 1,2-dimethoxyethane (300 mL) was gradually added diethyl cyanomethylphosphonate (19.7 g, 0.122 mol) at room temperature under an atmosphere of nitrogen gas. After stirring for 15 minutes, 5-bromo-2-methoxypyridine (20.0 g, 0.106 mol) and tetrakis(triphenylphosphine)palladium(0) (2.0 g, 1.73 mmol) were sequentially added thereto, and the mixture was heated to 90° C. and stirred for 6 hours. After standing to cool, the reaction mixture was further cooled on ice. 3-Fluorobenzaldehyde (13.7 g, 0.110 mol) was added dropwise thereinto under an atmosphere of nitrogen gas at 1° C. to 4° C. over 1.5 hours, and the mixture was stirred for further 2.5 hours while gradually elevating to room temperature. The reaction mixture was diluted with a saturated aqueous ammonium chloride solution and ethyl acetate, and then the aqueous layer was extracted with ethyl acetate. The combined organic layers were washed with a saturated aqueous ammonium chloride solution twice, dried over anhydrous sodium sulfate and then concentrated. The residue was suspended in methanol, and the resulting solid was collected by filtration and washed with diethyl ether and hexane, to give the title compound (7.80 g, 29%) as a colorless solid.

Provenance & Evidence