反应详情

To a cold solution of 6-bromo-2-methylpyrimidine-4-carbaldehyde oxime (0.4 g, 1.852 mmol Preparation #17) and styrene (0.257 mL, 2.222 mmol) in DCM (10 mL) was added sodium hypochlorite solution (0.229 mL, 3.70 mmol). The reaction mixture was stirred for about 2 h and diluted with DCM (50 mL), successively washed with water (2×30 mL) and brine (1×30 mL). The organic layer was dried over sodium sulphate and evaporated to dryness under reduced pressure. The resulting mixture was purified by silica gelchromatography eluting with 40% EtOAc in hexane. Relevant fractions containing the required compound were combined and evaporated to dryness under reduced pressure to afford 3-(6-bromo-2-methylpyrimidin-4-yl)-5-phenyl-4,5-dihydroisoxazol 0.25 g (42.4%), 1H NMR (400 MHz, DMSO): δ 8.00 (s, 1H), 7.40 (m, 5H), 5.90 (m, 1H), 3.93 (m, 1H), 3.41 (m, 1H), 2.64 (s, 3H), MS m/z: 320 (M+H)+.

1. washsuccessively washed with water (2×30 mL) and brine (1×30 mL)
2. dry with materialThe organic layer was dried over sodium sulphate
3. customevaporated to dryness under reduced pressure
4. customThe resulting mixture was purified by silica gelchromatography
5. washeluting with 40% EtOAc in hexane
6. additionRelevant fractions containing the required compound
7. customevaporated to dryness under reduced pressure