Ammonium Chloride → 1-[1-[[2-(Trimethylsilyl)ethoxy]methyl]-1H-pyrazol-4-yl]ethanone

HRID 2092053Notes

Reaction equation

HRID 2092053 reaction equation
CON(C)[C:4]([C:6]1[CH:7]=[N:8][N:9]([CH2:11][O:12][CH2:13][CH2:14][Si:15]([CH3:18])([CH3:17])[CH3:16])[CH:10]=1)=[O:5].[CH3:20][Mg]Br.[Cl-].[NH4+]>O1CCCC1>[CH3:18][Si:15]([CH3:16])([CH3:17])[CH2:14][CH2:13][O:12][CH2:11][N:9]1[CH:10]=[C:6]([C:4](=[O:5])[CH3:20])[CH:7]=[N:8]1

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 59574442HCID 59574442, compoundHCID 178418573HCID 178418573, compound

Product 1

HCID 595743441-[1-[[2-(Trimethylsilyl)ethoxy]methyl]-1H-pyrazol-4-yl]ethanoneYield 33%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

N-Methoxy-N-methyl-1-{[2-(trimethylsilyl)ethoxy]methyl}-1H-pyrazole-4-carboxamide (325.8 mg, 1.14 mmol) in tetrahydrofuran (2 mL) was mixed with methylmagnesium bromide (0.98 M in tetrahydrofuran, 4.32 mL, 4.23 mmol) under cooling with ice and the reaction mixture was warmed slowly to room temperature for 16 hours with stirring. After completion of the reaction, the reaction solution was mixed with saturated aqueous ammonium chloride, and extracted with ethyl acetate. The organic layer was dried over anhydrous sodium sulfate and evaporated under reduced pressure. The resulting residue was purified by silica gel column chromatography (hexane/ethyl acetate=2/1, to ethyl acetate/MeOH=20/1) to give the desired product (89.9 mg, 33% yield).

Workup

  1. temperatureunder cooling with ice
  2. customAfter completion of the reaction
  3. extractionextracted with ethyl acetate
  4. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  5. customevaporated under reduced pressure
  6. customThe resulting residue was purified by silica gel column chromatography (hexane/ethyl acetate=2/1, to ethyl acetate/MeOH=20/1)

Sources & evidence

ORD record
ord-14c8aa0e3068422ba2983957226a2595
Source dataset
uspto-grants-2013_05
Patent number
US08440666B2

Reaction notes

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