3-Hydroxypyridine → HCID 14986715, compound

Participants

Reaction Conditions

Reaction Steps

To a mixture of triphenylphosphine (2.42 g, 9.2 mmol) and 3-hydroxypyridine (0.7 g, 7.3 mmol) in methylene chloride (20 mL) is added the ethyl 7-cyano-5-hydroxyheptanoate obtained above. The reaction mixture is stirred for 5 minutes and then diethyl azodicarboxylate (1.0 mL, 6.3 mmol) is added dropwise. The reaction mixture is stirred overnight and the solvent is evaporated. The residue is chromatographed on silica gel using ether as eluent to obtain an amber oil. The oil is dissolved in 10 mL ether, cooled to 0° C. and the precipitated triphenylphosphine oxide is filtered off. The filtrate is evaporated to give crude ethyl 7-cyano-5-(3-pyridyloxy)-heptanoate, IR (CH2Cl2): 2239, 1729, 1576, 1229, 1167, 1120 cm-1.

Provenance & Evidence