반응 #160802

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

MCPBA

→

title compound

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

용매

CH2Cl2

반응 조건

후처리

1. 1
   기타The mixture was quenched with sat'd
2. 2
   기타The mixture was then partitioned between CH2Cl2
3. 3
   추출Extracted with CH2Cl2
4. 4
   기타The combined organics were dried
5. 5
   여과filtered
6. 6
   농축concentrated
7. 7
   기타The residue was purified by column chromatography

실험 절차

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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