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Potassium Carbonate → Diethyl 1-(2-{[tert-butyl(dimethyl)silyl]oxy}ethyl)-1H-pyrazole-3,5-dicarboxylate

HRID 1158874
Notes
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Reaction equation

HRID 1158874 reaction equation
[NH:1]1[C:5]([C:6]([O:8][CH2:9][CH3:10])=[O:7])=[CH:4][C:3]([C:11]([O:13][CH2:14][CH3:15])=[O:12])=[N:2]1.C(=O)([O-])[O-].[K+].[K+].Br[CH2:23][CH2:24][O:25][Si:26]([C:29]([CH3:32])([CH3:31])[CH3:30])([CH3:28])[CH3:27]>C(#N)C.C(OCC)(=O)C>[Si:26]([O:25][CH2:24][CH2:23][N:1]1[C:5]([C:6]([O:8][CH2:9][CH3:10])=[O:7])=[CH:4][C:3]([C:11]([O:13][CH2:14][CH3:15])=[O:12])=[N:2]1)([C:29]([CH3:32])([CH3:31])[CH3:30])([CH3:28])[CH3:27]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 142184diethyl 1H-pyrazole-3,5-dicarboxylateHCID 3608067(2-Bromoethoxy)-tert-butyldimethylsilane

Product 1

HCID 68444496Diethyl 1-(2-{[tert-butyl(dimethyl)silyl]oxy}ethyl)-1H-pyrazole-3,5-dicarboxylateYield 100.1%

Reagents, catalysts & solvents 2

HCID 6342Acetonitrile
Solvent
HCID 8857Ethyl AcetateSolvent

Procedure

To a solution of diethyl 3,5-pyrazoledicarboxylate (2.17 g, 10 mmol) in acetonitrile (10 ml), under nitrogen, was added potassium carbonate (2.07 g, 15 mmol), and 2-bromoethoxy-t-butyldimethylsilane (2.90 g, 12 mmol). The mixture was stirred at reflux for 18 hr. It was then cooled to room temperature, diluted with ethyl acetate (20 ml), and filtered through Magnesol. The filter pad was eluted with 2×10 ml of ethyl acetate, and the combined filtrate was evaporated. The residue was dissolved in hexanes and passed through a column of silica gel (70 g). After eluting with hexanes (100 ml), the column was eluted with ethyl acetate. The ethyl acetate eluent was evaporated to give 3.71 g of a colorless oil; MS m/e 371 (MH+).

Workup

  1. temperatureat reflux for 18 hr
  2. filtrationfiltered through Magnesol
  3. washThe filter pad was eluted with 2×10 ml of ethyl acetate
  4. customthe combined filtrate was evaporated
  5. dissolutionThe residue was dissolved in hexanes
  6. washAfter eluting with hexanes (100 ml)
  7. washthe column was eluted with ethyl acetate
  8. customThe ethyl acetate eluent was evaporated

Sources & evidence

ORD record
ord-dc0e98263b6d4278868b76463ebc9e62
Source dataset
uspto-grants-2010_10
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07812014B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes