Dimethyl Sulfide → HCID 14403426, compound

HRID 1650729Notes

Reaction equation

HRID 1650729 reaction equation
CSC.S([O:9][CH3:10])(OC)(=O)=O.[C:11]1([S:17][C:18]2([C:21]([CH2:23][CH2:24][C:25]3[CH:30]=[CH:29][C:28]([Cl:31])=[CH:27][CH:26]=3)=O)[CH2:20][CH2:19]2)[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.[OH-].[K+]>C(O)(C)(C)C>[Cl:31][C:28]1[CH:29]=[CH:30][C:25]([CH2:24][CH2:23][C:21]2([C:18]3([S:17][C:11]4[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=4)[CH2:20][CH2:19]3)[CH2:10][O:9]2)=[CH:26][CH:27]=1

Participants

6

Reactant 4

HCID 1068Dimethyl SulfideHCID 6497Dimethyl SulfateHCID 14797Potassium HydroxideHCID 14403425HCID 14403425, compound

Product 1

HCID 14403426HCID 14403426, compoundYield 82%

Reagents, catalysts & solvents 1

HCID 6386tert-ButanolSolvent2×

Procedure

21 ml (0.29 mol) o& dimethyl sulphide and 32.5 g (0.26 mol) of dimethyl sulphate are added to 40 ml of tert.-butanol and allowed to stand at room temperature for 14 hours. A solution of 30 g (0.095 mol) of 4-chlorophenylethyl 1-phenylmercapto-cyclopropyl ketone in 90 ml of tert.-butanol are first added dropwise to the reaction mixture with stirring and 29.2 g of potassium hydroxide powder are then introduced, while the temperature of the reaction mixture is held at 20 to 30° C. The mixture is stirred for a further 3 hours at 30° C., then the dimethyl sulphide is removed under reduced pressure and the reaction mixture is then poured into 70 ml of a 1% strength aqueous hydrogen peroxide solution. The mixture is extracted with ethyl acetate. The organic phase is washed with water and concentrated by removing the solvent under reduced pressure after drying over sodium sulphate. In this manner, 25.6 g (82% of theory) of 2-(4-chlorophenylethyl)-2-(1-phenylmercapto-cyclopropyl)oxirane are obtained in the form of an oily product which is reacted further without additional purification. ##STR68##

Workup

  1. customis held at 20 to 30° C
  2. stirringThe mixture is stirred for a further 3 hours at 30° C.
  3. customthe dimethyl sulphide is removed under reduced pressure
  4. additionthe reaction mixture is then poured into 70 ml of a 1% strength aqueous hydrogen peroxide solution
  5. extractionThe mixture is extracted with ethyl acetate
  6. washThe organic phase is washed with water
  7. concentrationconcentrated
  8. customby removing the solvent under reduced pressure
  9. dry with materialafter drying over sodium sulphate

Sources & evidence

ORD record
ord-fc1e29bcfb8645a1b8463a663c5c6c66
Source dataset
uspto-grants-1990_05
Patent number
US04925865

Reaction notes

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