Sodium borohydride → Ethyl 3-(2-chloropyridin-5-yl)propionate

HRID 53200Notes

Reaction equation

HRID 53200 reaction equation
[BH4-].[Na+].[Cl:3][C:4]1[CH:9]=[CH:8][C:7]([CH:10]=[CH:11][C:12]([O:14][CH2:15][CH3:16])=[O:13])=[CH:6][N:5]=1>C(O)C>[Cl:3][C:4]1[CH:9]=[CH:8][C:7]([CH2:10][CH2:11][C:12]([O:14][CH2:15][CH3:16])=[O:13])=[CH:6][N:5]=1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 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) of Te powder and 0.6 g (2 eq) of NaBH4 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-5yl)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-ec542c1c9b2a40199ac51be469a0f6be
Source dataset
uspto-grants-1997_04
Patent number
US05618821

Reaction notes

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