Sodium hydride → HCID 13013627, compound

HRID 1633377Notes

Reaction equation

HRID 1633377 reaction equation
[H-].[Na+].[I-].[CH3:4][S+](C)(C)=O.[H][H].[Cl:11][C:12]1[CH:31]=[CH:30][CH:29]=[CH:28][C:13]=1[C:14]([C:16]1[CH:21]=[CH:20][C:19]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)=[CH:18][CH:17]=1)=[O:15]>CS(C)=O.O>[C:19]1([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[CH:18]=[CH:17][C:16]([C:14]2([C:13]3[CH:28]=[CH:29][CH:30]=[CH:31][C:12]=3[Cl:11])[CH2:4][O:15]2)=[CH:21][CH:20]=1

Participants

7

Reactant 4

HCID 24758Sodium hydrideHCID 74498Sulfoxonium, trimethyl-, iodide (1:1)HCID 198145Methanone, (1,1-biphenyl)-4-yl(2-chlorophenyl)-HCID 178418361HCID 178418361, compound

Product 1

HCID 13013627HCID 13013627, compoundYield 65.2%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolvent

Conditions

Temperature
50 °C

Procedure

90 ml of dimethylsulphoxides are added to 2.7 g (0.09 mol) of 80% strength sodium hydride and 19.8 g (0.09 mol) of trimethyloxosulphonium iodide in the course of 20 minutes. When the evolution of hydrogen has ended, a solution of 22 g (0.075 mol) of 2-chloro-4'-phenyl-benzophenone in 60 ml of dimethylsulphoxide is added dropwise and the mixture is subsequently stirred at 50° C. for 1 hour. 200 ml of water are added to the cooled reaction mixture and the mixture is extracted by shaking with ether. The ether solution is washed with water, dried over sodium sulphate and concentrated by distilling off the solvent in vacuo. The residue is recrystallised from diisopropyl ether. 15 g (65% of theory) of 2-(4-biphenylyl)-2-(2-chlorophenyl)-oxirane of melting point 70° C. are obtained.

Workup

  1. extractionthe mixture is extracted
  2. stirringby shaking with ether
  3. washThe ether solution is washed with water
  4. dry with materialdried over sodium sulphate
  5. concentrationconcentrated
  6. distillationby distilling off the solvent in vacuo
  7. customThe residue is recrystallised from diisopropyl ether

Sources & evidence

ORD record
ord-53bc120665ba416a9e65de60152390a9
Source dataset
uspto-grants-1984_10
Patent number
US04480114

Reaction notes

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