Ammonium Chloride → HCID 89962338, compound

HRID 337967Notes

Reaction equation

HRID 337967 reaction equation
I[C:2]1[CH:3]=[N:4][N:5]([CH2:7][O:8][CH3:9])[CH:6]=1.C([Mg]Cl)(C)C.[F:15][C:16]1([F:23])[CH2:21][CH2:20][C:19](=[O:22])[CH2:18][CH2:17]1.[Cl-].[NH4+]>C1COCC1>[F:15][C:16]1([F:23])[CH2:21][CH2:20][C:19]([C:2]2[CH:3]=[N:4][N:5]([CH2:7][O:8][CH3:9])[CH:6]=2)([OH:22])[CH2:18][CH2:17]1

Participants

6

Reactant 4

HCID 25517Ammonium ChlorideHCID 10376890HCID 10376890, compoundHCID 157890924,4-DifluorocyclohexanoneHCID 178418918HCID 178418918, compound

Product 1

HCID 89962338HCID 89962338, compoundYield 66%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 4-iodo-1-(methoxymethyl)-1H-pyrazole (Organic Letters, 2007, 9, 4947-4950; 1.40 g, 5.88 mmol) in THF (15 mL), isopropyl magnesium chloride (2.0 M solution in THF; 3.8 mL, 7.64 mmol) was added with cooling on ice. The reaction solution was stirred for 30 minutes with cooling on ice. Then, 4,4-difluorocyclohexanone (2.30 g, 17.6 mmol) was added thereto, and the mixture was stirred at room temperature for 1 hour. To the reaction solution, an aqueous ammonium chloride solution (50 mL) was added, followed by extraction with ethyl acetate (50 mL). The thus obtained organic layer was dried over anhydrous sodium sulfate. After vacuum concentration, the residue was purified with silica gel chromatography (hexane/ethyl acetate=7:3) to yield the title compound (0.95 g, 66%) as a colorless oil.

Workup

  1. temperaturewith cooling on ice
  2. temperaturewith cooling on ice
  3. stirringthe mixture was stirred at room temperature for 1 hour
  4. extractionfollowed by extraction with ethyl acetate (50 mL)
  5. dry with materialThe thus obtained organic layer was dried over anhydrous sodium sulfate
  6. concentrationAfter vacuum concentration
  7. customthe residue was purified with silica gel chromatography (hexane/ethyl acetate=7:3)

Sources & evidence

ORD record
ord-3915db60149a410e831ff013b111a798
Source dataset
uspto-grants-2014_11
Patent number
US08889741B2

Reaction notes

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