Ethyl bromopyruvate → 2-Methylpentane

HRID 2390538Notes

Reaction equation

HRID 2390538 reaction equation
Br[CH2:2][C:3](=O)[C:4]([O:6][CH2:7][CH3:8])=[O:5].[CH3:10][C:11]([CH3:16])([CH3:15])[C:12](=[S:14])[NH2:13]>C(O)C.CCOC(C)=O>[CH3:10][CH2:11][CH2:12][CH:3]([CH3:2])[CH3:4].[C:11]([C:12]1[S:14][CH:2]=[C:3]([C:4]([O:6][CH2:7][CH3:8])=[O:5])[N:13]=1)([CH3:16])([CH3:15])[CH3:10]

Participants

6

Reactant 2

HCID 66144Ethyl bromopyruvateHCID 30311302,2-Dimethylpropanethioamide

Product 2

HCID 78922-MethylpentaneHCID 58790291Ethyl 2-(tert-butyl)thiazole-4-carboxylate

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

Ethyl 3-bromo-2-oxopropanoate (6.20 mL, 49.40 mmol) was added very carefully to a stirred solution of 2,2-dimethylpropanethioamide (5.79 g, 49.40 mmol) in ethanol (60 mL). The solution was then heated under reflux for 16 h. After cooling, the reaction mixture was diluted with EtOAc, washed with saturated aqueous sodium bicarbonate solution and evaporated in vacuo. Purification by silica gel chromatography (Biotage, 100 g) eluting with EtOAc: iso-hexane, 1:10 gave the sub-title compound as a yellow oil. Yield: 6.56 g

Workup

  1. temperatureThe solution was then heated
  2. temperatureunder reflux for 16 h
  3. temperatureAfter cooling
  4. washwashed with saturated aqueous sodium bicarbonate solution
  5. customevaporated in vacuo
  6. customPurification by silica gel chromatography (Biotage, 100 g)
  7. washeluting with EtOAc

Sources & evidence

ORD record
ord-21c25ab50d2a4c8bb9ed9ec9ca00b3dc
Source dataset
uspto-grants-2012_09
Patent number
US08273774B2

Reaction notes

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