Ethyl bromopyruvate → 2-Methylpentane

HRID 471174Notes

Reaction equation

HRID 471174 reaction equation
Br[CH2:2][C:3](=O)[C:4]([O:6][CH2:7][CH3:8])=[O:5].[C:10](=[S:16])([NH2:15])[CH2:11][CH2:12][CH2:13][CH3:14]>C(O)C.C(OCC)(=O)C>[CH3:10][CH2:11][CH2:12][CH:3]([CH3:2])[CH3:4].[CH2:11]([C:10]1[S:16][CH:2]=[C:3]([C:4]([O:6][CH2:7][CH3:8])=[O:5])[N:15]=1)[CH2:12][CH2:13][CH3:14]

Participants

6

Reactant 2

HCID 66144Ethyl bromopyruvateHCID 12534254Pentanethioamide

Product 2

HCID 78922-MethylpentaneHCID 67292599Ethyl 2-butyl-1,3-thiazole-4-carboxylate

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

Ethyl 3-bromo-2-oxopropanoate (6.76 mL) was added very carefully to a stirred solution of pentanethioamide (example 78, step e) (6.30 g) in ethanol (100 mL). The solution was then heated at reflux for 16 h. After cooling, the reaction mixture was diluted with ethyl acetate, washed with saturated sodium bicarbonate solution and evaporated in vacuo. Purification by silica gel chromatography eluting with 1:6 ethyl acetate: isohexane gave the subtitled compound as a yellow oil. Yield 6.5 g.

Workup

  1. temperatureThe solution was then heated
  2. temperatureat reflux for 16 h
  3. temperatureAfter cooling
  4. washwashed with saturated sodium bicarbonate solution
  5. customevaporated in vacuo
  6. customPurification by silica gel chromatography
  7. washeluting with 1:6 ethyl acetate

Sources & evidence

ORD record
ord-6b24fbfd0712456cb89faa5955478e9e
Source dataset
uspto-grants-2014_01
Patent number
US08629271B2

Reaction notes

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