Ethyl Acetate → HCID 12397257, compound

Participants

Reaction Steps

To a stirred solution of 5-benzyloxy-6-hydroxymethyl-2-pyridinecarboxaldehyde (5.86 g., 0.0241 mol) in 100 ml. of ethyl acetate is added 4.056 g. (0.0265 mol) of phosphorus oxychloride and the mixture is refluxed for 20 minutes. Additional phosphorus oxychloride (0.4 ml.) is introduced and the mixture is heated further for 30 minutes. The reaction mixture is cooled, diluted with ether and then washed with 5% sodium bicarbonate solution and brine. The ethereal solution is dried, treated with charcoal, filtered and evaporated to leave an oil which crystallizes to give 5-benzyloxy-6-chloromethyl-2-pyridinecarboxaldehyde, m.p. 72°-73°C.

Provenance & Evidence