Reacción #486517

Ecuación de reacción

2e

1,3-dichloro-3-fluoro-7-oxabicyclo[4.1.0]heptane

alcohol

1-vinyl-2,2,6.6-tetrachlorocyclohexanol

sodium hydroxide

→

epoxide

Rendimiento 90.0%

1,3,3-trichloro-2-vinyl-7-oxabicyclo[4.1.0]heptane

Rendimiento 90.0%

Disolventes

water

Condiciones de reacción

Tratamiento posterior

1. 1
   Otroreaction time
2. 2
   Extracciónether extraction (4×25 cm3)
3. 3
   Otropurified by flash chromatography on silica (eluent: ether/petroleum ether=3/97)

Procedimiento

The same procedure was employed as for the preparation of 2e in Example 17: it was performed with 1.14 g (4.32 mmol) of pure alcohol 1k, 12 cm3 of distilled water and 0.5 g (12.5 mmol) of sodium hydroxide; reaction time was 1 h 15 min; ether extraction (4×25 cm3); the crude product was employed as such (crude yld=90.5%) or purified by flash chromatography on silica (eluent: ether/petroleum ether=3/97): 0.88 g of epoxide 2i were obtained, that was a 90% yield (macrobore GC purity>98.6%) MW: 227.519; 1H NMR: 6.75-6.30 (m, 1H); 5.80-5.45 (m, 2H); 3.00-1.25 (m, 6H). 13C NMR: 126.1 (C7); 123.1 (C8); 88.35 (C3); 85.5 (C1); 70.0 (C2); 39.75 (C4); 32.4 (C6); 18.3 (C5). IR in cm-1 (film): 1080-940-875-785-735.

Fuente