tert-Butyl bromoacetate → 1793069-27-8

HRID 2279926Notes

Reaction equation

HRID 2279926 reaction equation
[NH:1]1[CH:5]=[C:4]([CH:6]=[O:7])[CH:3]=[N:2]1.CC(C)([O-])C.[K+].[C:14]([O:18][C:19](=[O:22])[CH2:20]Br)([CH3:17])([CH3:16])[CH3:15]>CN(C)C=O>[CH:6]([C:4]1[CH:5]=[N:1][N:2]([CH2:20][C:19]([O:18][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:22])[CH:3]=1)=[O:7]

Participants

5

Reactant 3

HCID 79177tert-Butyl bromoacetateHCID 51306731H-pyrazole-4-carbaldehydeHCID 23665647Potassium tert-butoxide

Product 1

HCID 889754691793069-27-8Yield 62%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 1H-pyrazole-4-carbaldehyde (0.5 g, 5.2 mmol), potassium tert-butoxide (0.7 g, 6.25 mmol) in N,N-dimethylformamide (6 mL) was stirred at room temperature for 5 minutes. Tert-butylbromoacetate (1.11 g, 5.72 mmol) was added and the resulting mixture was stirred for 2 hours at room temperature. The reaction was partitioned between ethyl acetate and saturated aqueous sodium bicarbonate solution. The organic layer was collected, washed with water then brine, passed through a hydrophobic fit and the solvent was removed in vacuo. The crude material was purified by silica gel column chromatography, eluting with 15-100% ethyl acetate in iso-hexane, to afford the title compound (0.678 g, 62%) as colorless oil.

Workup

  1. stirringthe resulting mixture was stirred for 2 hours at room temperature
  2. customThe reaction was partitioned between ethyl acetate and saturated aqueous sodium bicarbonate solution
  3. customThe organic layer was collected
  4. washwashed with water
  5. customthe solvent was removed in vacuo
  6. customThe crude material was purified by silica gel column chromatography
  7. washeluting with 15-100% ethyl acetate in iso-hexane

Sources & evidence

ORD record
ord-26775aef4c254ca6b0e4e630bd9ff92a
Source dataset
uspto-grants-2015_09
Patent number
US09133185B2

Reaction notes

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