Reacción #160813

Ecuación de reacción

3,4,4a,5,6,7-hexahydro-1H-isochromene

MCPBA

→

title compound

(1aS,5aS)-hexahydro-4H-oxireno[i]isochromene

Disolventes

CH2Cl2

Condiciones de reacción

Tratamiento posterior

1. 1
   OtroIt was quenched with sat'd aq. sodium sulfite
2. 2
   workup.ADDITIONThe mixture was diluted with CH2Cl2
3. 3
   Extracciónaq. NaHCO3 then extracted 3× with CH2Cl2
4. 4
   SecadoThe combined organics were dried (anhd. Na2SO4)
5. 5
   Filtraciónfiltered
6. 6
   Concentraciónconcentrated
7. 7
   OtroThe residue was purified by column chromatography

Procedimiento

To a mixture of 3,4,4a,5,6,7-hexahydro-1H-isochromene (0.410 g, 2.97 mmol) in CH2Cl2 (10 mL) at 0° C. was added MCPBA (˜77%, 1.24 g, 445 mmol). The mixture was stirred at rt for 3 hr. It was quenched with sat'd aq. sodium sulfite. The mixture was diluted with CH2Cl2 and sat'd. aq. NaHCO3 then extracted 3× with CH2Cl2. The combined organics were dried (anhd. Na2SO4), filtered, and concentrated. The residue was purified by column chromatography to give the title compound. 1H NMR (500 MHz, CDCl3) δ 4.03-4.10 (m, 1H), 3.86 (d, 1H, J=12.0 Hz), 3.54-3.62 (m, 1H), 3.34 (d, 1H, J=12.0 Hz), 3.03 (d, 1H, J=4.4 Hz), 1.70-1.98 (m, 3H), 1.52-1.65 (m, 3H), 1.17-1.34 (m, 3H).

Fuente