Sodium hydride → HCID 131729527, compound

HRID 1095931Notes

Reaction equation

HRID 1095931 reaction equation
[C:1]([SiH2:5][O:6][C:7]([CH3:14])([CH3:13])[C:8]1[CH:9]=[N:10][NH:11][CH:12]=1)([CH3:4])([CH3:3])[CH3:2].[H-].[Na+].[CH3:17][O:18][C:19](=[O:22])[CH2:20]Br>CN(C=O)C>[CH3:17][O:18][C:19](=[O:22])[CH2:20][N:10]1[CH:9]=[C:8]([C:7]([CH3:14])([CH3:13])[O:6][SiH2:5][C:1]([CH3:4])([CH3:2])[CH3:3])[CH:12]=[N:11]1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 60984Methyl bromoacetateHCID 131729528HCID 131729528, compound

Product 1

HCID 131729527HCID 131729527, compoundYield 98%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
0 °C

Procedure

4-(tert-Butyl-dimethyl-silanyloxymethyl)-1H-pyrazole (348 mg) was dissolved in DMF (12 mL) and cooled to 0° C. To this solution was added NaH (60% in mineral oil, 111 mg). The mixture was stirred at 0° C. for 30 minutes and then methylbromoacetate (0.23 mL) was added dropwise. The mixture was stirred at r.t. overnight. The reaction mixture was poured into ice/water and extracted with chloroform. The combined organic layers were washed with brine, dried over Na2SO4, filtered and the solvent was evaporated. The residue was purified by flash chromatography (silica gel, heptane:ethyl acetate=100:0 to 0:100) to give the title compound as a yellow oil (484 mg, 98%). MS (m/e)=285.0 [MH+].

Workup

  1. stirringThe mixture was stirred at r.t. overnight
  2. extractionextracted with chloroform
  3. washThe combined organic layers were washed with brine
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. customthe solvent was evaporated
  7. customThe residue was purified by flash chromatography (silica gel, heptane:ethyl acetate=100:0 to 0:100)

Sources & evidence

ORD record
ord-bcf48136460748fe9f41722e5cd22bdc
Source dataset
uspto-grants-2012_03
Patent number
US08138189B2

Reaction notes

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