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

HRID 73616

反応式

HRID 73616 の反応式
[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]

参加物

3

反応物 2

HCID 9246Cyclohexene oxideHCID 693893-Buten-1-ol

生成物 1

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

反応条件

温度
0 °C

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-d972889f7d7a40909401873c2d5988f0
出典データセット
uspto-grants-2014_09
特許番号
US08829196B2

関連ノート

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