(E)-Ethyl 3-(6-chloropyridin-3-YL)acrylate → Ethyl 3-(2-chloropyridin-5-yl)propionate

HRID 963308Notes

Reaction equation

HRID 963308 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]=[CH:9][C:10]([O:12][CH2:13][CH3:14])=[O:11])=[CH:4][N:3]=1>C(O)C>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][C:10]([O:12][CH2:13][CH3:14])=[O:11])=[CH:4][N:3]=1

Participants

3

Reactant 1

HCID 53406713(E)-Ethyl 3-(6-chloropyridin-3-YL)acrylate

Product 1

HCID 19082020Ethyl 3-(2-chloropyridin-5-yl)propionateYield 84%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A suspension of 0.84 g (1 eq) or Te powder and 0.6 g (2 eq) of NaEH4 in 32 ml of ethanol was heated under nitrogen until it became a homogeneous purple solution. To the above hot solution was added ethyl β-(2-chloropyridin-5-yl)acrylate (1.38 g, 6.5 mmol) and the mixture was refluxed for 4 h. The crude product was purified by flash chromatography (silica gel; hexane/ethyl acetate, 3:1) to afford 1.11 g (84,6%) of ethyl 3-(2-chloropyridin-5-yl)propionate.

Workup

  1. temperaturewas heated under nitrogen until it
  2. temperaturethe mixture was refluxed for 4 h
  3. customThe crude product was purified by flash chromatography (silica gel; hexane/ethyl acetate, 3:1)

Sources & evidence

ORD record
ord-3d9819c7f88f431d82be4d4ef89b0e4e
Source dataset
uspto-grants-1998_06
Patent number
US05763461

Reaction notes

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