Reacción #62244

Ecuación de reacción

4-allylanisole

3-chloroperoxybenzoic acid

→

2-(4-Methoxybenzyl)-oxirane

Disolventes

dichloromethane

Condiciones de reacción

Tratamiento posterior

1. 1
   Otroafter 3 h
2. 2
   OtroThe precipitate was removed via filtration
3. 3
   Lavadowashed with hexanes
4. 4
   OtroThe filtrate was purified on 40 g silica eluting with 0 to 10% ethyl acetate/hexanes
5. 5
   Otroto give the product

Procedimiento

To a stirring solution of 4-allylanisole (3.1 g, 20.9 mmol) in 50 mL dichloromethane was added 3-chloroperoxybenzoic acid (80%, 6.7 g, 31.4 mmol) at room temperature. TLC (20:1 hexanes/ethyl acetate) showed no remaining allyl after 3 h. The precipitate was removed via filtration and washed with hexanes. The filtrate was purified on 40 g silica eluting with 0 to 10% ethyl acetate/hexanes to give the product. NMR CDCl3) d (1H, 2.55 ppm), m (2H, 2.7-2.8 ppm), dd (1H, 2.85 ppm), m (1H, 3.1 ppm), s (3H, 3.75 ppm), d (2H, 6.85 ppm), d (2H, 7.15 ppm).

Fuente