Potassium Carbonate → 1-[2-(4-tert-butyl-phenyl)-2-oxo-ethyl]-1H-pyrazole-3,5-dicarboxylic acid diethyl ester

HRID 2272952Notes

Reaction equation

HRID 2272952 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.Br[CH2:17][C:18]([C:20]1[CH:25]=[CH:24][C:23]([C:26]([CH3:29])([CH3:28])[CH3:27])=[CH:22][CH:21]=1)=[O:19].C(=O)([O-])[O-].[K+].[K+]>CC(C)=O>[CH2:9]([O:8][C:6]([C:5]1[CH:4]=[C:3]([C:11]([O:13][CH2:14][CH3:15])=[O:12])[N:2]([CH2:17][C:18]([C:20]2[CH:25]=[CH:24][C:23]([C:26]([CH3:29])([CH3:28])[CH3:27])=[CH:22][CH:21]=2)=[O:19])[N:1]=1)=[O:7])[CH3:10]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 142184diethyl 1H-pyrazole-3,5-dicarboxylateHCID 23247702-Bromo-1-(4-tert-butylphenyl)ethan-1-one

Product 1

HCID 898321591-[2-(4-tert-butyl-phenyl)-2-oxo-ethyl]-1H-pyrazole-3,5-dicarboxylic acid diethyl ester

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A solution of 849 mg (4.00 mmol) diethyl pyrazole-3,5-dicarboxylate and 1.02 g (4.00 mmol) 2-bromo-1-(4-tert-butyl-phenyl)-ethanone in 4 ml acetone is treated with 663 mg (4.80 mmol) potassium carbonate. The resulting suspension is stirred overnight at room temperature. The reaction mixture is partitioned between water and dichloromethane. The organic phase is dried over sodium sulfate and evaporated to give 1-[2-(4-tert-butyl-phenyl)-2-oxoethyl]-1H-pyrazole-3,5-dicarboxylic acid diethyl ester as light yellow foam; HPLC/MS 2.77 (A), [M+H] 387.

Workup

  1. customThe reaction mixture is partitioned between water and dichloromethane
  2. dry with materialThe organic phase is dried over sodium sulfate
  3. customevaporated

Sources & evidence

ORD record
ord-51afb1646a694c9c8bde1f93671bab3e
Source dataset
uspto-grants-2015_09
Patent number
US09120805B2

Reaction notes

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