1-(3-Hydroxy-4-methoxyphenyl)ethanone → 5-[(E)-N-[(3-fluorophenyl)methoxy]-C-methylcarbonimidoyl]-2-methoxyphenol

Participants

Reaction Steps

Acetophenone 12 (50 mg, 0.301 mmol) was condensed with O-(3-fluorobenzyl)hydroxylamine hydrochloride (26) (59 mg, 0.332 mmol) according to the general procedure II-B defined above. After being heated at reflux for 48 h the reaction mixture was cooled and the solvent removed under reduced pressure. The ensuing residue was dissolved in CH2Cl2 (15 mL), washed with H2O (2×10 mL) then dried (MgSO4), filtered and concentrated under reduced pressure. The oil thus obtained was subjected to flash chromatography (1:19 v/v ethyl acetate/hexane elution) to afford the title compound CP30262 (71 mg, 82%) as a pale-pink oil, Rf 0.6 in 1:1 v/v ethyl acetate/hexane.

Provenance & Evidence