Cyclohexene oxide → 2-(But-3-en-1-yloxy)cyclohexanol

HRID 73616

반응식

HRID 73616 반응식
[CH:1]12[O:7][CH:2]1[CH2:3][CH2:4][CH2:5][CH2:6]2.[CH2:8]([OH:12])[CH2:9][CH:10]=[CH2:11]>>[CH2:8]([O:12][CH:2]1[CH2:3][CH2:4][CH2:5][CH2:6][CH:1]1[OH:7])[CH2:9][CH:10]=[CH2:11]

참가 물질

3

반응물 2

HCID 9246Cyclohexene oxideHCID 693893-Buten-1-ol

생성물 1

HCID 665775152-(But-3-en-1-yloxy)cyclohexanol

반응 조건

온도
0 °C

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).

후처리

  1. customwas removed from the ice bath
  2. customThe reaction was quenched with water
  3. extractionextracted ether
  4. washThe combined organics were washed with brine
  5. customdried
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe residue was purified by column chromatography

출처 및 근거

ORD 기록
ord-d972889f7d7a40909401873c2d5988f0
출처 데이터셋
uspto-grants-2014_09
특허 번호
US08829196B2

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