Water → 5-(4-Chlorophenyl)-4-(pyridin-4-yl)-1-(2-trimethylsilylethoxy)methylpyrazole

HRID 9883Notes

Reaction equation

HRID 9883 reaction equation
[H-].[Na+].[Cl:3][C:4]1[CH:9]=[CH:8][C:7]([C:10]2[NH:14][N:13]=[CH:12][C:11]=2[C:15]2[CH:20]=[CH:19][N:18]=[CH:17][CH:16]=2)=[CH:6][CH:5]=1.[CH3:21][Si:22]([CH3:29])([CH3:28])[CH2:23][CH2:24][O:25][CH2:26]Cl.O>O1CCCC1>[Cl:3][C:4]1[CH:5]=[CH:6][C:7]([C:10]2[N:14]([CH2:26][O:25][CH2:24][CH2:23][Si:22]([CH3:29])([CH3:28])[CH3:21])[N:13]=[CH:12][C:11]=2[C:15]2[CH:20]=[CH:19][N:18]=[CH:17][CH:16]=2)=[CH:8][CH:9]=1

Participants

6

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 27242712-Chloromethyl 2-(trimethylsilyl)ethyl etherHCID 219885015-(4-Chlorophenyl)-4-(pyridin-4-yl)pyrazole

Product 1

HCID 219884875-(4-Chlorophenyl)-4-(pyridin-4-yl)-1-(2-trimethylsilylethoxy)methylpyrazoleYield 90%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

55% Sodium hydride (1.41 g, 32.1 mmol) was suspended in tetrahydrofuran (300 ml). To the suspension was added 5-(4-chlorophenyl)-4-(pyridin-4-yl)pyrazole (8.21 g, 32.1 mmol), and the resulting mixture was stirred at room temperature for 1 hour. To the resulting mixture was added (2-trimethylsilylethoxy)methyl chloride (5.68 ml, 32.1 mmol) dropwise under ice cooling, and the mixture was stirred at room temperature overnight. At the end of this time, water was added to the mixture and the mixture was extracted with ethyl acetate. The organic layer was washed with water, dried over anhydrous sodium sulfate and the solvent was removed by distillation under reduced pressure. The residue was purified by column chromatography through silica gel (eluent, hexane:ethyl acetate=3:1), to give the title compound (11.12 g) as a pale brown oil (yield 90%).

Workup

  1. stirringthe mixture was stirred at room temperature overnight
  2. extractionthe mixture was extracted with ethyl acetate
  3. washThe organic layer was washed with water
  4. dry with materialdried over anhydrous sodium sulfate
  5. customthe solvent was removed by distillation under reduced pressure
  6. customThe residue was purified by column chromatography through silica gel (eluent, hexane:ethyl acetate=3:1)

Sources & evidence

ORD record
ord-03390b047e824451a249e4a8748421c9
Source dataset
uspto-grants-2006_08
Patent number
US07091352B2

Reaction notes

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