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

Participants

Reaction Steps

Acetophenone 12 (50 mg, 0.301 mmol) was condensed with O-(4-fluorobenzyl)hydroxylamine hydrochloride (29) (58 mg, 0.327 mmol) according to the general procedure II-B defined above. After being heated for 24 h the reaction mixture was cooled and the solvent removed under reduced pressure. The ensuing residue was dissolved in CH2Cl2 (15 mL) and the resulting solution 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 CP30266 (70 mg, 80%) as a pale-purple waxy-oil, Rf 0.5 in 1:1 v/v ethyl acetate/hexane.

Provenance & Evidence