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

HRID 2263606Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2263606
[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

Komponenten

6

Edukt 4

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

Produkt 1

HCID 686846494-Cyclopropylmethanesulfonyl-1-cyclopropylmethylcyclohex-3-enecarbonitrileAusbeute 93 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel2×

Versuchsvorschrift

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).

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-3e44f56e4a794d978b56c62b5bf42549
Quelldatensatz
uspto-grants-2010_12
Patentnummer
US07851638B2

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