Methyl iodide → HCID 20131579, compound

HRID 845567Notes

Reaction equation

HRID 845567 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].[CH3:14]I>O1CCCC1>[F:1][C:2]([N:9]1[CH:13]=[N:12][CH:11]=[N:10]1)([C:3](=[O:8])[C:4]([CH3:7])([CH3:5])[CH3:6])[CH3:14]

Participants

4

Reactant 2

HCID 6328Methyl iodideHCID 13021647HCID 13021647, compound

Product 1

HCID 20131579HCID 20131579, compoundYield 65.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

20.0 g of 1-fluoro-1-(1H-1,2,4-triazol-1-yl)-3,3-dimethyl-2-butanone are added dropwise to a solution of 13.5 g of potassium tertiary butylate in 100 ml of tetrahydrofuran. After the mixture has been stirred for 0.5 hour, 15.6 g of methyl iodide are added dropwise and the mixture is stirred for 18 hours at 60° C. After cooling, the reaction 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 14.0 g of 2-fluoro-2-(1H-1,2,4-triazol-1-yl)-4,4-dimethyl-3-pentanone, boiling point 48°-50° C./0.013 mbar.

Workup

  1. stirringthe mixture is stirred for 18 hours at 60° C
  2. temperatureAfter cooling
  3. extractionextracted with ethyl acetate
  4. washThe combined organic phases are washed with water and saturated sodium chloride solution
  5. dry with materialdried over sodium sulfate
  6. customevaporated
  7. distillationDistillation of the oily residue

Sources & evidence

ORD record
ord-161e274492244bc58981affa7d0d5c44
Source dataset
uspto-grants-1988_07
Patent number
US04758670

Reaction notes

Loading…