반응 #160798

반응 방정식

cyclohexene oxide

3-buten-1-ol

→

title compound

2-(but-3-en-1-yloxy)cyclohexanol

반응 조건

후처리

1. 1
   기타was removed from the ice bath
2. 2
   기타The reaction was quenched with water
3. 3
   추출extracted ether
4. 4
   세척The combined organics were washed with brine
5. 5
   기타dried
6. 6
   여과filtered
7. 7
   농축concentrated
8. 8
   기타The residue was purified by column chromatography

실험 절차

To a mixture of cyclohexene oxide (3-1) (10.0 g, 102 mmol) in 3-buten-1-ol (17.4 mL, 204 mmol) cooled to 0° C. was added FeCl3 (1.65 g, 10.2 mol) The mixture was removed from the ice bath and stirred at rt for 1 hr. The reaction was quenched with water and extracted ether. The combined organics were washed with brine, dried, filtered, and concentrated. The residue was purified by column chromatography to give the title compound. 1H NMR (400 MHz, CDCl3) δ 5.77-5.88 (m, 1H), 5.00-5.15 (m, 2H), 3.69-3.76 (m, 1H), 3.39-3.44 (m, 2H), 2.98-3.05 (m, 1H), 2.74 (s, 1H), 2.30-2.39 (m, 2H), 1.94-2.11 (m, 3H), 1.61-1.79 (m, 3H), 1.06-1.37 (m, 2H).

출처