Water → 2-(4-Chlorophenoxymethyl)-2-(2,2-difluoro-1-methylcyclopropyl)-oxirane

HRID 728036

Reaction equation

HRID 728036 reaction equation
C[O-].[Na+].[CH3:4][O:5]S([O-])(=O)=O.C[S+](C)C.[Cl:14][C:15]1[CH:30]=[CH:29][C:18]([O:19][CH2:20][C:21]([C:23]2([CH3:28])[CH2:25][C:24]2([F:27])[F:26])=O)=[CH:17][CH:16]=1.O>C(#N)C>[Cl:14][C:15]1[CH:16]=[CH:17][C:18]([O:19][CH2:20][C:21]2([C:23]3([CH3:28])[CH2:25][C:24]3([F:26])[F:27])[CH2:4][O:5]2)=[CH:29][CH:30]=1

Participants

6

Reactant 4

HCID 962WaterHCID 2760871Trimethylsulfonium methyl sulfateHCID 10942334Sodium MethoxideHCID 146952401-(4-Chlorophenoxyacetyl)-1-methyl-2,2-difluorocyclopropane

Product 1

HCID 146952412-(4-Chlorophenoxymethyl)-2-(2,2-difluoro-1-methylcyclopropyl)-oxirane

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

2.4 g (0.044 mol) of sodium methoxide are added to the solution of 30 ml (0.04 mol) of a 1.36-molar solution of trimethylsulphonium methylsulphate in acetonitrile, and the mixture is stirred at room temperature for 30 minutes. 5.8 g (0.022 mol) of 1-(4-chlorophenoxyacetyl)-1-methyl-2,2-difluorocyclopropane are then added, and the mixture is stirred for 16 hours at 20° C. The reaction mixture is poured into 200 ml of water and extracted using methylene chloride, and the organic phase is washed with water and concentrated. 4.3 g (GC content of 73%; 71.6% of theory) of 2-(4-chlorophenoxymethyl)-2-(2,2-difluoro-1-methylcyclopropyl)-oxirane are obtained as a viscous resin which is reacted further directly. ##STR79##

Workup

  1. stirringthe mixture is stirred for 16 hours at 20° C
  2. extractionextracted
  3. washthe organic phase is washed with water
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-8573277f0284485aa2b75c76d01aa420
Source dataset
uspto-grants-1991_09
Patent number
US05047415

Linked notes

Loading…