Dimethyl Sulfide → HCID 14348395, compound

HRID 1650726Notes

Reaction equation

HRID 1650726 reaction equation
CSC.S([O:9][CH3:10])(OC)(=O)=O.[Cl:11][C:12]1[CH:17]=[CH:16][C:15]([CH2:18][CH2:19][C:20]([C:22]2([Cl:25])[CH2:24][CH2:23]2)=O)=[CH:14][CH:13]=1.[OH-].[K+]>C(O)(C)(C)C>[Cl:25][C:22]1([C:20]2([CH2:19][CH2:18][C:15]3[CH:14]=[CH:13][C:12]([Cl:11])=[CH:17][CH:16]=3)[CH2:10][O:9]2)[CH2:23][CH2:24]1

Participants

6

Reactant 4

HCID 1068Dimethyl SulfideHCID 6497Dimethyl SulfateHCID 14797Potassium HydroxideHCID 14403422HCID 14403422, compound

Product 1

HCID 14348395HCID 14348395, compoundYield 75%

Reagents, catalysts & solvents 1

HCID 6386tert-ButanolSolvent2×

Procedure

16 ml (0.22 mol) of dimethyl sulphide and 24.2 g (0.19 mol) of dimethyl sulphate are added to 30 ml of tert.-butanol and allowed to stand at 20° C. for 14 hours. A solution of 17 g (0.07 mol) of 1-chlorocyclopropyl 4-chlorophenylethyl ketone in 70 ml of tert.-butanol is first added dropwise to the reaction mixture with stirring and 22 g of potassium hydroxide powder are then introduced, while the temperature of the reaction mixture is kept at 20° to 30° C. The mixture is stirred at 30° C. for 3 hours more, then the dimethyl sulphide is removed under reduced pressure and the reaction mixture is then poured into 50 ml of a 1% 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, 13.4 g (75 % of theory) of 2-(1-chlorocyclopropyl)-2-(4-chlorophenylethyl)-oxirane are obtained in the form of an oily product, which is reacted further without additional purification. ##STR64##

Workup

  1. customis kept at 20° to 30° C
  2. stirringThe mixture is stirred at 30° C. for 3 hours more
  3. customthe dimethyl sulphide is removed under reduced pressure
  4. additionthe reaction mixture is then poured into 50 ml of a 1% 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-689d192d09304321b173e7d6ef3916e6
Source dataset
uspto-grants-1990_05
Patent number
US04925865

Reaction notes

Loading…