Ethyl 4-Cyanocinnamate → Ethyl 3-(4-cyanophenyl)propanoate

HRID 1978398Notes

Reaction equation

HRID 1978398 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][C:6](/[CH:9]=[CH:10]/[C:11]([O:13][CH2:14][CH3:15])=[O:12])=[CH:5][CH:4]=1)#[N:2]>O1CCCC1.[C].[Pd]>[C:1]([C:3]1[CH:8]=[CH:7][C:6]([CH2:9][CH2:10][C:11]([O:13][CH2:14][CH3:15])=[O:12])=[CH:5][CH:4]=1)#[N:2]

Participants

4

Reactant 1

HCID 5373497Ethyl 4-Cyanocinnamate

Product 1

HCID 11435631Ethyl 3-(4-cyanophenyl)propanoateYield 98%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 8028TetrahydrofuranSolvent

Procedure

(E)-Ethyl 3-(4-cyanophenyl)acrylate (13.9 g, 69.1 mmol) in tetrahydrofuran (100 ml) was hydrogenated over 10% Palladium-Carbon (4.00 g) at atmospheric pressure. After removal of the catalyst, the filtrate was concentrated in vacuo to give ethyl 3-(4-cyanophenyl)propionate as a yellow oil (13.7 g, 98%).

Workup

  1. customAfter removal of the catalyst
  2. concentrationthe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-47a823ce45b04071b23fd26f4489f254
Source dataset
uspto-grants-2001_05
Patent number
US06235731B1

Reaction notes

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