Dimethyl Sulfoxide → HCID 14798965, compound

HRID 345866Notes

Reaction equation

HRID 345866 reaction equation
CS(C)=O.[H-].[Na+].[I-].C[S+](C)(C)=[O:10].C(C1(C2C=C(F)C=C[C:19]=2[C:25]([C:27]2[CH:32]=[CH:31][C:30]([F:33])=[CH:29][C:28]=2[C:34]2([C:37]#[N:38])[CH2:36][CH2:35]2)=O)CC1)#N>O>[C:37]([C:34]1([C:28]2([C:27]3[CH:25]=[CH:19][C:30]([F:33])=[CH:31][CH:32]=3)[CH2:29][O:10]2)[CH2:35][CH2:36]1)#[N:38]

Participants

6

Reactant 4

HCID 679Dimethyl SulfoxideHCID 24758Sodium hydrideHCID 74498Sulfoxonium, trimethyl-, iodide (1:1)HCID 53747917HCID 53747917, compound

Product 1

HCID 14798965HCID 14798965, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
20 °C

Procedure

130 ml of abs. DMSO are slowly added dropwise at 10° C. to 6.6 g (0.22 mol) of sodium hydride (80% in oil) and 34.2 g (0.16 mol) of trimethylsulphoxonium iodide. The mixture is stirred for one hour at 20° C. and then 26.3 g (0.14 mol) of 1-cyanocyclopropyl-4-fluorophenyl ketone (compound II-2, Example 19, dissolved in 65 ml of abs. DMSO) are added dropwise. The mixture is stirred for 14 h at 20° C. The solution is poured into water and the mixture is extracted with ethyl acetate. The combined organic phases are washed with H2O and dried over Na2SO4, and the solvent is evaporated in vacuo. The residue is chromatographed on silica gel and 15 g (54% of theory) of 2-(1-cyanocyclopropyl)-2-(4-fluorophenyl)oxirane are obtained in the form of a colorless oil after evaporating the solvent, 1H--NMR (CDCl3):

Workup

  1. stirringThe mixture is stirred for 14 h at 20° C
  2. extractionthe mixture is extracted with ethyl acetate
  3. washThe combined organic phases are washed with H2O
  4. dry with materialdried over Na2SO4
  5. customthe solvent is evaporated in vacuo
  6. customThe residue is chromatographed on silica gel and 15 g (54% of theory) of 2-(1-cyanocyclopropyl)-2-(4-fluorophenyl)oxirane
  7. customare obtained in the form of a colorless oil
  8. customafter evaporating the solvent, 1H

Sources & evidence

ORD record
ord-04f2e0721eff41b495b8ed5585f4c0cb
Source dataset
uspto-grants-1991_10
Patent number
US05059615

Reaction notes

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