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

HRID 2263606Notes

Reaction equation

HRID 2263606 reaction equation
[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

Participants

6

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

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).

Workup

  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

Sources & evidence

ORD record
ord-3e44f56e4a794d978b56c62b5bf42549
Source dataset
uspto-grants-2010_12
Patent number
US07851638B2

Reaction notes

Loading…