Réaction #160802

Équation de réaction

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

MCPBA

→

title compound

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

Solvants

CH2Cl2

Conditions de réaction

Traitement

1. 1
   AutreThe mixture was quenched with sat'd
2. 2
   AutreThe mixture was then partitioned between CH2Cl2
3. 3
   ExtractionExtracted with CH2Cl2
4. 4
   AutreThe combined organics were dried
5. 5
   Filtrationfiltered
6. 6
   Concentrationconcentrated
7. 7
   AutreThe residue was purified by column chromatography

Mode opératoire

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).

Source