Sodium hydride → HCID 66584862, compound

HRID 2368973Notes

Reaction equation

HRID 2368973 reaction equation
[CH3:1][C:2]1([CH3:14])[C:6]([CH3:8])([CH3:7])[O:5][B:4]([C:9]2[CH:13]=[CH:12][NH:11][N:10]=2)[O:3]1.[H-].[Na+].[CH3:17][Si:18]([CH2:21][CH2:22][O:23][CH2:24]Cl)([CH3:20])[CH3:19]>C1COCC1.O>[CH3:1][C:2]1([CH3:14])[C:6]([CH3:7])([CH3:8])[O:5][B:4]([C:9]2[CH:13]=[CH:12][N:11]([CH2:24][O:23][CH2:22][CH2:21][Si:18]([CH3:20])([CH3:19])[CH3:17])[N:10]=2)[O:3]1

Participants

6

Reactant 3

HCID 24758Sodium hydrideHCID 27242712-Chloromethyl 2-(trimethylsilyl)ethyl etherHCID 178431094HCID 178431094, compound

Product 1

HCID 66584862HCID 66584862, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

At 0° C., 3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole (388 mg, 2 mmoL) was added to NaH (160 mg, 60%, 4 mmoL) in THF (12 mL). After stirring at room temperature for 30 min, the mixture was cooled to 0° C. and SEMCl (705.7 μL, 4 mmoL) was added. The mixture was stirred at room temperature overnight, diluted with H2O and then extracted with ethyl acetate (×2). The combined organic layers were washed with brine and dried with Na2SO4. Evaporation afforded crude 3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-pyrazole.

Workup

  1. temperaturethe mixture was cooled to 0° C.
  2. stirringThe mixture was stirred at room temperature overnight
  3. extractionextracted with ethyl acetate (×2)
  4. washThe combined organic layers were washed with brine
  5. dry with materialdried with Na2SO4
  6. customEvaporation

Sources & evidence

ORD record
ord-0589941597304c5eaf57296a80c7d3de
Source dataset
uspto-grants-2014_04
Patent number
US08703784B2

Reaction notes

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