反应详情

To sodium brohydride suspended (0.177 g, 4.7 mmol) in methanol (15 ml) under cooling with ice was slowly added dropwise 3-dimethylamino-5-(1-(3-benzoylphenyl) ethyl)-1,2,4-oxadiazole (1.45 g, 4.5 mmol) in methanol (15 ml). After the mixture was stirred under cooling with ice with 1 h, 1N-HCl was added to the mixture, then the mixture was adjusted at pH 6. The mixture was evaporated under reduced pressure to a residue, which was extracted with dichloromethane. The extracts were washed with saturated NaCl aq., dried with anhydrous magnesium sulfate, and evaporated under reduced pressure to a residue, which was chlomatographed to afford 3-dimethylamino-5-(1-(3-(α-hydroxybenzyl)phenyl)ethyl)- 1,2,4-oxadiazole (1.50 g, 99% yield) as oily substance: NMR(CDCl3)δ1.45(d, 3H), 2.27(d, 1H), 3.00(s, 6H), 4.20(q, 1H), 5.80(d, 1H), 7.20-7.45 m(m, 9H) ppm; IR(neat) 3375, 1600, 1405 cm-1.

1. temperatureunder cooling with ice
2. temperatureunder cooling with ice with 1 h
3. customThe mixture was evaporated under reduced pressure to a residue, which
4. extractionwas extracted with dichloromethane
5. washThe extracts were washed with saturated NaCl aq.
6. dry with materialdried with anhydrous magnesium sulfate
7. customevaporated under reduced pressure to a residue, which