O-Methylhydroxylamine → Furo[2,3-b]pyridin-3(2H)-one O-methyloxime

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Reaction Steps

To a solution of furo[2,3-b]pyridine-3(2H)-one (78.3 mmol) [J. Heterocyclic Chem., 23, 1465 (1986)] in 500 mL EtOH were added O-methyl-hydroxylamine (157 mmol) and NaOAc (157 mmol). After heating to reflux for 2 h the reaction mixture was concentrated in vacuo to half of its volume. Water and DCM were added and the aqueous phase was extracted 3 times with DCM. The combined organic layers were dried over MgSO4 and concentrated in vacuo. Purification by CC using Hept/EtOAc (5/1 to 1/1) gives the desired product as yellow oil;

Provenance & Evidence