反应详情

To 3-(4-isobutyl-3-(trifluoromethyl)phenyl)-7-vinyl-4,5-dihydronaphtho[1,2-c]isoxazole (Preparation 23C, 0.3 g, 0.755 mmol) in THF (2 mL) was sequentially added N-methylmorpholine N-oxide (50% in water) (0.35 mL, 0.755 mmol) and osmium tetroxide (4% in water) (0.118 mL, 0.015 mmol) at room temperature. The reaction mixture was stirred at room temperature for 60 h. Next, sodium periodate (0.242 g, 1.132 mmol) dissolved in 1.5 mL of water was added at room temperature. The heterogeneous reaction mixture was stirred at room temperature for 30 min. and the reaction mixture was partitioned between ethyl acetate (10 mL) and brine (5 mL). The ethyl acetate layer was dried over sodium sulfate and concentrated to yield 3-(4-isobutyl-3-(trifluoromethyl)phenyl)-4,5-dihydronaphtho[1,2-c]isoxazole-7-carbaldehyde (0.3 g, 0.751 mmol, 100% yield) as an off-white solid. LC/MS M+1=400.2.

1. customat room temperature
2. additionwas added at room temperature
3. stirringThe heterogeneous reaction mixture was stirred at room temperature for 30 min.
4. customthe reaction mixture was partitioned between ethyl acetate (10 mL) and brine (5 mL)
5. dry with materialThe ethyl acetate layer was dried over sodium sulfate
6. concentrationconcentrated