Sodium hydride → HCID 70497804, compound

HRID 1466642Notes

Reaction equation

HRID 1466642 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([O:18][CH:19]2[CH2:21][CH2:20]2)=[C:6]([C:8]2[C:12]([C:13]([O:15][CH2:16][CH3:17])=[O:14])=[CH:11][NH:10][N:9]=2)[CH:7]=1.[H-].[Na+].[CH3:24][Si:25]([CH2:28][CH2:29][O:30][CH2:31]Cl)([CH3:27])[CH3:26]>C1COCC1>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([O:18][CH:19]2[CH2:21][CH2:20]2)=[C:6]([C:8]2[N:9]([CH2:31][O:30][CH2:29][CH2:28][Si:25]([CH3:27])([CH3:26])[CH3:24])[N:10]=[CH:11][C:12]=2[C:13]([O:15][CH2:16][CH3:17])=[O:14])[CH:7]=1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 27242712-Chloromethyl 2-(trimethylsilyl)ethyl etherHCID 178469916HCID 178469916, compound

Product 1

HCID 70497804HCID 70497804, compoundYield 93.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of ethyl 3-(5-chloro-2-cyclopropoxyphenyl)-1H-pyrazole-4-carboxylate (12 g, 39 mmol) in THF (200 mL) was added 60% sodium hydride in mineral oil (1.72 g, 43 mmol) and the reaction mixture was stirred for 10 min. SEMCl (7.2 g, 43 mmol) was added and the reaction mixture was stirred at room temperature overnight. The mixture was quenched with ice-water and extracted with EtOAc (300 mL×2). The combined organics were dried over sodium sulfate and concentrated in vacuo afford 16 g of the title compounds.

Workup

  1. stirringthe reaction mixture was stirred at room temperature overnight
  2. customThe mixture was quenched with ice-water
  3. extractionextracted with EtOAc (300 mL×2)
  4. dry with materialThe combined organics were dried over sodium sulfate
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-167d677f377f432e8ce07a9ad154bc97
Source dataset
uspto-grants-2015_04
Patent number
US08999998B2

Reaction notes

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