Acetone → 4-Cyclopropylmethanesulfonyl-1-cyclopropylmethylcyclohex-3-enecarbonitrile

HRID 1865463ノート

反応式

HRID 1865463 の反応式
[CH:1]1([CH2:4][C:5]2([C:16]#[N:17])[CH2:10][CH2:9][C:8](SCC3CC3)=[CH:7][CH2:6]2)[CH2:3][CH2:2]1.O[O:19][S:20]([O-:22])=O.[K+].[C:24](=O)([O-])O.[Na+].[CH3:29][C:30]([CH3:32])=O>O>[CH:30]1([CH2:32][S:20]([C:8]2[CH2:9][CH2:10][C:5]([CH2:4][CH:1]3[CH2:3][CH2:2]3)([C:16]#[N:17])[CH2:6][CH:7]=2)(=[O:22])=[O:19])[CH2:24][CH2:29]1

参加物

6

反応物 4

HCID 180AcetoneHCID 516892Sodium BicarbonateHCID 23707502Potassium hydroxy sulfiteHCID 686840531-Cyclopropylmethyl-4-cyclopropylmethylsulfanylcyclohex-3-enecarbonitrile

生成物 1

HCID 686846494-Cyclopropylmethanesulfonyl-1-cyclopropylmethylcyclohex-3-enecarbonitrile収率 93%

試薬・触媒・溶媒 1

HCID 962Water溶媒2 回

実験手順

A solution of 1-cyclopropylmethyl-4-cyclopropylmethylsulfanylcyclohex-3-enecarbonitrile (10.7 g, 43.1 mmol) in acetone (200 ml) was treated with a solution of oxone (79.4 g, 129 mmol) in water (300 ml) and the mixture heated under reflux for 1 h. The mixture was allowed to cool to ambient temperature and the pH of the mixture adjusted to 7 by the addition of saturated sodium hydrogen carbonate solution. The mixture was diluted with water (200 ml) and extracted with ethyl acetate (2×400 ml). The combined organic layer was washed with water (250 ml) and brine (200 ml), dried over anhydrous sodium sulphate, filtered and evaporated to give a white solid (11.2 g, 93%). 1H NMR δ (ppm)(CDCl3): 6.91 (1H, s), 2.98-2.74 (4H, m), 2.66-2.53 (1H, m), 2.42-2.25 (2H, m), 1.71-1.67 (3H, m), 1.13-1.05 (1H, m), 0.97-0.87 (1H, m), 0.73-0.59 (4H, m), 0.45-0.35 (2H, m), 0.23-0.18 (2H, m).

後処理

  1. temperaturethe mixture heated
  2. temperatureunder reflux for 1 h
  3. extractionextracted with ethyl acetate (2×400 ml)
  4. washThe combined organic layer was washed with water (250 ml) and brine (200 ml)
  5. dry with materialdried over anhydrous sodium sulphate
  6. filtrationfiltered
  7. customevaporated

出典と根拠

ORDレコード
ord-2de95c5e3bbb4ad9871efcdf8b134b5f
出典データセット
uspto-grants-2009_12
特許番号
US07626056B2

反応ノート

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