Реакция #160802

Уравнение реакции

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

MCPBA

→

title compound

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

Растворители

CH2Cl2

Условия реакции

Обработка

1. 1
   ДругоеThe mixture was quenched with sat'd
2. 2
   ДругоеThe mixture was then partitioned between CH2Cl2
3. 3
   ЭкстракцияExtracted with CH2Cl2
4. 4
   ДругоеThe combined organics were dried
5. 5
   Фильтрацияfiltered
6. 6
   Концентрированиеconcentrated
7. 7
   ДругоеThe residue was purified by column chromatography

Методика

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).

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