Ethyl benzylidenecyanoacetate → Ethyl 2-cyano-3-phenylpropanoate

HRID 1607388

Reaction equation

HRID 1607388 reaction equation
[CH2:1]([O:3][C:4](=[O:15])[C:5]([C:13]#[N:14])=[CH:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)[CH3:2]>C1C=CC=CC=1.[Pd]>[CH2:1]([O:3][C:4](=[O:15])[CH:5]([C:13]#[N:14])[CH2:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)[CH3:2]

Participants

4

Reactant 1

HCID 74845Ethyl benzylidenecyanoacetate

Product 1

HCID 228103Ethyl 2-cyano-3-phenylpropanoateYield 92.5%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 241BenzeneSolvent

Procedure

A solution of 4.56 g of the ester obtained in 30 ml of benzene was hydrogenated over 0.45 g of a 10% palladium/charcoal under a hydrogen atmosphere at room temperature for 4 hours. After filtration of the catalyst, the reaction mixture was concentrated under reduced pressure to obtain 4.26 g of 2-cyano-3-phenylpropionic acid ethyl ester as a colorless oil.

Workup

  1. filtrationAfter filtration of the catalyst
  2. concentrationthe reaction mixture was concentrated under reduced pressure

Sources & evidence

ORD record
ord-c3f8c538c3994304819a7c2b309f2c97
Source dataset
uspto-grants-1989_09
Patent number
US04863904

Linked notes

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