Dimethyl Sulfoxide → HCID 20131577, compound

HRID 845568Notes

Reaction equation

HRID 845568 reaction equation
[F:1][C:2]([N:10]1[CH:14]=[N:13][CH:12]=[N:11]1)([C:4](=[O:9])[C:5]([CH3:8])([CH3:7])[CH3:6])[CH3:3].[I-].[CH3:16][S+](C)(C)=O.CS(C)=O>O1CCCC1>[C:5]([C:4]1([C:2]([F:1])([N:10]2[CH:14]=[N:13][CH:12]=[N:11]2)[CH3:3])[CH2:16][O:9]1)([CH3:8])([CH3:6])[CH3:7]

Participants

5

Reactant 3

HCID 679Dimethyl SulfoxideHCID 74498Sulfoxonium, trimethyl-, iodide (1:1)HCID 20131579HCID 20131579, compound

Product 1

HCID 20131577HCID 20131577, compoundYield 46.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
80 °C

Procedure

12.0 g of 2-fluoro-2-(1H-1,2,4-triazol-1-yl)-4,4-dimethyl-3-pentanone are added dropwise to a mixture of 13.2 g of trimethylsulfoxonium iodide, 7.3 g of potassium tertiary butylate, 20 ml of dimethyl sulfoxide and 80 ml of tetrahydrofuran, and the reaction mixture is stirred for 18 hours at 80° C. After cooling, the mixture is taken up in ice water and extracted with ethyl acetate. The combined organic phases are washed with water and saturated sodium chloride solution, dried over sodium sulfate and evaporated. Distillation of the oily residue gives 6 g 2-tert.-butyl-2-[1-fluoro-1-(1H-1,2,4-triazol-1-yl)-ethyl]-oxirane, boiling point 60°-61° C./0.013 mbar.

Workup

  1. temperatureAfter cooling
  2. extractionextracted with ethyl acetate
  3. washThe combined organic phases are washed with water and saturated sodium chloride solution
  4. dry with materialdried over sodium sulfate
  5. customevaporated
  6. distillationDistillation of the oily residue

Sources & evidence

ORD record
ord-752d225d6a9e470d9da412860e8bea50
Source dataset
uspto-grants-1988_07
Patent number
US04758670

Reaction notes

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