Tert-butyl 3-(4-cyano-3-methylphenyl)acrylate → Tert-butyl 3-(4-cyano-3-methylphenyl)propanoate

HRID 1820950Notes

Reaction equation

HRID 1820950 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([CH:10]=[CH:11][C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])[CH:5]=[CH:6][C:7]=1[C:8]#[N:9].[H][H]>[Pd].CCOC(C)=O>[CH3:1][C:2]1[CH:3]=[C:4]([CH2:10][CH2:11][C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])[CH:5]=[CH:6][C:7]=1[C:8]#[N:9]

Participants

5

Reactant 2

HCID 68649265Tert-butyl 3-(4-cyano-3-methylphenyl)acrylateHCID 178418361HCID 178418361, compound

Product 1

HCID 68649344Tert-butyl 3-(4-cyano-3-methylphenyl)propanoateYield 99.7%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 5.0 g (20.6 mmol) of tert-butyl 3-(3-methyl-4-cyanophenyl)acrylate (from Step A) and 500 mg of 10% palladium on carbon in 200 mL of EtOAc was stirred under 1 atm of hydrogen at rt for 16 h. The catalyst was removed by filtration. The filtrate was concentrated to afford 5.04 g of the title compound: 1H NMR (500 MHz, CDCl3) δ 1.42 (s, 9H), 2.53 (s, 3H), 2.55 (t, J=7.6, 2H), 2.93 (t, J=7.6, 2H), 7.12 (d, J=7.8, 1H), 7.17 (s, 1H), 7.51 (d, J=7.8, 1H).

Workup

  1. customThe catalyst was removed by filtration
  2. concentrationThe filtrate was concentrated

Sources & evidence

ORD record
ord-9cfdcf026cbd4f3a968ea66a32477831
Source dataset
uspto-grants-2009_10
Patent number
US07605171B2

Reaction notes

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