Reaktion #160808

Reaktionsgleichung

3,5,6,7,8,8a-hexahydro-1H-isochromene

MCPBA

→

title compound

Octahydrooxireno[d]isochromene

Lösungsmittel

CH2Cl2

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeIt was quenched with sated aq. sodium sulfite
2. 2
   workup.ADDITIONThe mixture was diluted with CH2Cl2
3. 3
   Extraktionaq. NaHCO3 then extracted 3× with CH2Cl2
4. 4
   TrocknenThe combined organics were dried (anhd. Na2SO4)
5. 5
   Filtrationfiltered
6. 6
   Einengenconcentrated
7. 7
   SonstigeThe residue was purified by column chromatography

Vorschrift

To a mixture of 3,5,6,7,8,8a-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 sated 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.

Quelle