Sodium Sulfite → 7-(Oxiran-2-yl)-3-(5-phenyl-4-(trifluoromethyl)isoxazol-3-yl)-4,5-dihydronaphtho[1,2-c]isoxazole

To a solution of 3-(5-phenyl-4-(trifluoromethyl)isoxazol-3-yl)-7-vinyl-4,5-dihydronaphtho[1,2-c]isoxazole (Preparation 6A, 0.09 g, 0.220 mmol) in dichloromethane (5 mL) was added 3-chlorobenzoperoxoic acid (0.109 g, 0.441 mmol) at room temperature. The reaction mixture was stirred at room temperature for 1.5 h. Next, 3 mL of 10% sodium sulfite solution was added to the reaction mixture at room temperature and the contents were stirred for 10 min. The reaction mixture was concentrated and partitioned between ethyl acetate (10 mL) and sat. aq. sodium bicarbonate (2×10 mL). The ethyl acetate layer was dried over sodium sulfate and concentrated to yield a pale yellow solid. LC/MS M+1=425.

1. stirringthe contents were stirred for 10 min
2. concentrationThe reaction mixture was concentrated
3. custompartitioned between ethyl acetate (10 mL) and sat. aq. sodium bicarbonate (2×10 mL)
4. dry with materialThe ethyl acetate layer was dried over sodium sulfate
5. concentrationconcentrated
6. customto yield a pale yellow solid

ORD record

ord-271f3407c9cb4d4ea36413d1074d1a82

Source dataset

uspto-grants-2015_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09216972B2