反应详情

(±)-3-(2,4-Dihydroxyphenyl)cyclohexanone (22 mg), methoxylamine hydrochloride (18 mg) and sodium acetate (18 mg) were heated under reflux in ethanol. After 6 hr, further methoxylamine (36 mg) and sodium acetate (36 mg) were added and the mixture heated under reflux for a further 1 hr. The reaction mixture was evaporated in vacuo and the residue was partitioned between ethyl acetate (20 ml) and water (20 ml). The aqueous layer was extracted with ethyl acetate (2×20 ml), and the combined organic extracts were dried over magnesium sulfate and evaporated in vacuo. The crude residue was purified by flash column chromatography (SiO2, ethyl acetate/petrol, 1:1 v/v) to furnish the title compound as a mixture of isomers (18 mg, 72%). δH(CDCl3) 1.5-2.2 (6H, overlapping m), 2.42 (0.5H, bd), 2.69 (0.5H, bd), 2.92 (0.5H, m), 3.06 (0.5H, m), 3.24-3.38 (1H, m), 3.81 (1.5H, s), 3.88 (1.5H, s), 5.42 (0.5H, bs), 5.47 (0.5H, bs), 6.28-6.42 (2H, overlapping m), 6.86 (0.5H, bs), 6.98 (1H, m), 7.06 (0.5H, bs); m/z (ES−) 469 (2M−1)−.

1. temperaturethe mixture heated
2. temperatureunder reflux for a further 1 hr
3. customThe reaction mixture was evaporated in vacuo
4. customthe residue was partitioned between ethyl acetate (20 ml) and water (20 ml)
5. extractionThe aqueous layer was extracted with ethyl acetate (2×20 ml)
6. dry with materialthe combined organic extracts were dried over magnesium sulfate
7. customevaporated in vacuo
8. customThe crude residue was purified by flash column chromatography (SiO2, ethyl acetate/petrol, 1:1 v/v)