Tetrahydrofuran → HCID 20131574, compound

HRID 845565Notes

Reaction equation

HRID 845565 reaction equation
[F:1][CH:2]([N:9]1[CH:13]=[N:12][CH:11]=[N:10]1)[C:3](=[O:8])[C:4]([CH3:7])([CH3:6])[CH3:5].[I-].[CH3:15][S+](C)(C)=O.O1CCCC1>CS(C)=O>[C:4]([C:3]1([CH:2]([N:9]2[CH:13]=[N:12][CH:11]=[N:10]2)[F:1])[CH2:15][O:8]1)([CH3:7])([CH3:5])[CH3:6]

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 74498Sulfoxonium, trimethyl-, iodide (1:1)HCID 13021647HCID 13021647, compound

Product 1

HCID 20131574HCID 20131574, compoundYield 32.1%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
60 °C

Procedure

A mixture of 20 g of 1-fluoro-1-(1H-1,2,4-triazol-1-yl)-3,3-dimethyl-2-butanone, 13.5 g of potassium tertiary butylate, 24.0 g of trimethylsulfoxonium iodide, 80 ml of tetrahydrofuran and 20 ml of dimethyl sulfoxide is stirred at 60° C. for 6 hours. The reaction mixture is then 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. Crystallisation from petroleum ether gives 6.9 g of 2-tert.-butyl-2-[(1H-1,2,4-triazol-1-yl)-fluoromethyl]-oxirane, melting point 72°-74° C.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe combined organic phases are washed with water and saturated sodium chloride solution
  3. dry with materialdried over sodium sulfate
  4. customevaporated
  5. customCrystallisation from petroleum ether

Sources & evidence

ORD record
ord-744359229e0f4e64b37728f849fedf63
Source dataset
uspto-grants-1988_07
Patent number
US04758670

Reaction notes

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