Tetrahydrofuran → HCID 86684881, compound

HRID 238383Notes

Reaction equation

HRID 238383 reaction equation
C(=O)([O-])[O-].[K+].[K+].O1CCCC1.[CH3:12][N:13]1[C:17]([C:18]2[CH:23]=[CH:22][C:21]([C:24]([F:27])([F:26])[F:25])=[CH:20][CH:19]=2)=[C:16]([C:28]#[C:29][Si](C)(C)C)[CH:15]=[N:14]1>CO>[C:28]([C:16]1[CH:15]=[N:14][N:13]([CH3:12])[C:17]=1[C:18]1[CH:19]=[CH:20][C:21]([C:24]([F:27])([F:26])[F:25])=[CH:22][CH:23]=1)#[CH:29]

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 11430Potassium CarbonateHCID 86684880HCID 86684880, compound

Product 1

HCID 86684881HCID 86684881, compoundYield 86.3%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Under cooling in an ice bath, potassium carbonate (148 mg) was added to a tetrahydrofuran (16 mL) and methanol (36 mL) solution of 1-methyl-5-[4-(trifluoromethyl)phenyl]-4-[(trimethylsilyl)ethynyl]-1H-pyrazole (3.45 g), and the obtained solution was then stirred for 4.5 hours. Thereafter, the reaction solution was filtrated with Celite, and the filtrate was then concentrated under a reduced pressure. The residue was diluted with ethyl acetate, and was then washed with a saturated ammonium chloride aqueous solution. The organic layer was dried over anhydrous sodium sulfate, and was then concentrated under a reduced pressure. The residue was purified by column chromatography (silica gel 60N, hexane:ethyl acetate=85:15 to 60:40), so as to obtain the title compound (2.31 g).

Workup

  1. temperatureUnder cooling in an ice bath
  2. filtrationThereafter, the reaction solution was filtrated with Celite
  3. concentrationthe filtrate was then concentrated under a reduced pressure
  4. additionThe residue was diluted with ethyl acetate
  5. washwas then washed with a saturated ammonium chloride aqueous solution
  6. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  7. concentrationwas then concentrated under a reduced pressure
  8. customThe residue was purified by column chromatography (silica gel 60N, hexane:ethyl acetate=85:15 to 60:40)

Sources & evidence

ORD record
ord-b4a97cb77ef441c59631dae948b46c07
Source dataset
uspto-grants-2014_02
Patent number
US08642626B2

Reaction notes

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