Reaktion #160802

Reaktionsgleichung

3,5,6,7,8,8a-hexahydro-2H-chromene

MCPBA

→

title compound

(1aS,8aS)-hexahydro-1aH,4aH-oxireno[d]chromene

Lösungsmittel

CH2Cl2

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeThe mixture was quenched with sat'd
2. 2
   SonstigeThe mixture was then partitioned between CH2Cl2
3. 3
   ExtraktionExtracted with CH2Cl2
4. 4
   SonstigeThe combined organics were dried
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-2H-chromene (3.27 g, 23.66 mmol) in CH2Cl2 (75 mL) at 0° C. was added MCPBA (˜77%, 6.53 g, 28.4 mmol). The mixture was warmed to rt and stirred for 1 hr. The mixture was quenched with sat'd. aq. Na2SO3. The mixture was then partitioned between CH2Cl2 and sat'd. aq. NaHCO3. Extracted with CH2Cl2. The combined organics were dried, filtered, and concentrated. The residue was purified by column chromatography to give the title compound. 1H NMR (500 MHz, CDCl3) δ 3.85 (dd, 1H, J=7.8 Hz, 11.7 Hz), 3.54 (dd, 1H, J=4.6 Hz, 11.7 Hz), 3.31-3.38 (m, 1H), 3.19 (d, 1H, J=5.13 Hz), 2.15-2.24 (m, 1H), 1.75-1.97 (m, 4H), 1.52-1.72 (iii, 3H), 1.37-1.49 (m, 1H), 1.30-1.38 (m, 1H).

Quelle