Dimethyl Sulfide → HCID 13254742, compound

HRID 1087704Notes

Reaction equation

HRID 1087704 reaction equation
CSC.S([O:9][CH3:10])(OC)(=O)=O.[C:11]1([C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[CH:16]=[CH:15][C:14]([O:17][CH2:18][C:19](=O)[C:20]([CH3:24])([CH3:23])[CH:21]=[CH2:22])=[CH:13][CH:12]=1.C[O-].[Na+]>C(#N)C>[C:11]1([C:26]2[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=2)[CH:12]=[CH:13][C:14]([O:17][CH2:18][C:19]2([C:20]([CH3:24])([CH3:23])[CH:21]=[CH2:22])[CH2:10][O:9]2)=[CH:15][CH:16]=1

Participants

6

Reactant 4

HCID 1068Dimethyl SulfideHCID 6497Dimethyl SulfateHCID 10942334Sodium MethoxideHCID 13254741HCID 13254741, compound

Product 1

HCID 13254742HCID 13254742, compoundYield 80.4%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent3×

Procedure

A solution of 41.9 ml (0.567 mol) of dimethyl sulphide in 50 ml of acetonitrile was added dropwise to a solution of 49.4 ml (0.518 mol) of dimethyl sulphate in 250 ml of acetonitrile at 25° C., in the course of 2 hours, with external cooling. After the mixture had stood for 4 days at room temperature, 87.4 g (0.31 mol) of 5-(biphenyl-4-yloxy)-3,3-dimethylpent-1-en-4-one, dissolved in 90 ml of acetonitrile, were stirred in in the course of 1 hour. Thereafter, 31.6 g (0.58 mol) of sodium methylate were introduced at 25° C. After the mixture had been stirred for twelve hours at room temperature, the precipitated salt was filtered off, and the filtrate was concentrated. The oily residue was taken up in 500 ml of ethyl acetate, and the solution was washed with twice 500 ml of water and dried over anhydrous sodium sulphate. After the solution had been concentrated in vacuo, 73.4 g (80.4% of theory) of 2-(biphenyl-4-yloxymethyl)-2-(3,3-dimethylprop-1-en-3-yl)-oxirane were obtained as a colorless waxy mass. ##STR23##

Workup

  1. stirringAfter the mixture had been stirred for twelve hours at room temperature
  2. filtrationthe precipitated salt was filtered off
  3. concentrationthe filtrate was concentrated
  4. washthe solution was washed with twice 500 ml of water
  5. dry with materialdried over anhydrous sodium sulphate
  6. concentrationAfter the solution had been concentrated in vacuo

Sources & evidence

ORD record
ord-7a5a941620fc49d8898b7b1b745a29aa
Source dataset
uspto-grants-1990_10
Patent number
US04960456

Reaction notes

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