Benzyl Chloride → ethyl beta-(N-benzyl-2-oxo-4-pyridyl)propionate

HRID 1719545Notes

Reaction equation

HRID 1719545 reaction equation
[Na].[OH:2][C:3]1[CH:8]=[C:7]([CH2:9][CH2:10][C:11]([O:13][CH2:14][CH3:15])=[O:12])[CH:6]=[CH:5][N:4]=1.[CH2:16](Cl)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1>C(O)C>[CH2:16]([N:4]1[CH:5]=[CH:6][C:7]([CH2:9][CH2:10][C:11]([O:13][CH2:14][CH3:15])=[O:12])=[CH:8][C:3]1=[O:2])[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

Participants

5

Reactant 3

HCID 7503Benzyl ChlorideHCID 5360545SodiumHCID 178471091HCID 178471091, compound

Product 1

HCID 20267143ethyl beta-(N-benzyl-2-oxo-4-pyridyl)propionateYield 81.7%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent3×

Procedure

To a cooled solution of sodium (3.25 g) in ethanol (75 ml) was added a solution of ethyl β-(2-hydroxy-4-pyridyl)propionate (25.38 g) in ethanol (150 ml). This mixture was stirred for 45 minutes and then benzyl chloride (16.58 g) in ethanol (125 ml) was added. The reaction mixture was stirred under reflux for 9 hours, allowed to cool and evaporated under reduced pressure. The residue was taken up in water (150 ml) and diethyl ether (150 ml), the aqueous layer was separated and washed with diethyl ether (2×120 ml). The combined ether extracts were washed with water, dried over MgSO4 and evaporated under reduced pressure to yield ethyl β-(N-benzyl-2-oxo-4-pyridyl)propionate (30.29 g) as an oil.

Workup

  1. stirringThe reaction mixture was stirred
  2. temperatureunder reflux for 9 hours
  3. temperatureto cool
  4. customevaporated under reduced pressure
  5. customdiethyl ether (150 ml), the aqueous layer was separated
  6. washwashed with diethyl ether (2×120 ml)
  7. washThe combined ether extracts were washed with water
  8. dry with materialdried over MgSO4
  9. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-69cf92e90f6941d68c65af8494c2ec28
Source dataset
uspto-grants-1985_09
Patent number
US04540699

Reaction notes

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