Citric Acid → (5-{[6-(5-Methyl-1,2,4-oxadiazol-3-yl)pyridin-3-yl]oxy}-2-nitrophenyl)methanol

Participants

Reaction Steps

282 mg of N,N′-carboxydiimidazole was added to a tetrahydrofuran (5 ml) solution of 399 mg of the above carboxylic acid, and stirred at room temperature for 30 minutes. With cooling with ice, the above reaction liquid was added to an aqueous 5 ml solution of 219 mg of sodium borohydride, and stirred for 20 minutes. This was neutralized with aqueous 10% citric acid solution added thereto, then extracted with ethyl acetate, the organic layer was dried, and the solvent was evaporated away under reduced pressure to obtain 367 mg of (5-{[6-(5-methyl-1,2,4-oxadiazol-3-yl)pyridin-3-yl]oxy}-2-nitrophenyl)methanol as a pale yellow solid.

Provenance & Evidence