methyl (E)-3-(4-cyanophenyl)prop-2-enoate → Methyl 3-(4-cyanophenyl)propanoate

HRID 1591Notes

Reaction equation

HRID 1591 reaction equation
[C:1]([C:3]1[CH:14]=[CH:13][C:6](/[CH:7]=[CH:8]/[C:9]([O:11][CH3:12])=[O:10])=[CH:5][CH:4]=1)#[N:2]>C1(C)C=CC=CC=1.[Pd].[O-]S([O-])(=O)=O.[Ba+2]>[C:1]([C:3]1[CH:14]=[CH:13][C:6]([CH2:7][CH2:8][C:9]([O:11][CH3:12])=[O:10])=[CH:5][CH:4]=1)#[N:2]

Participants

4

Reactant 1

HCID 11106082methyl (E)-3-(4-cyanophenyl)prop-2-enoate

Product 1

HCID 14218717Methyl 3-(4-cyanophenyl)propanoateYield 77%

Reagents, catalysts & solvents 2

HCID 16218511Pd barium sulfateCatalystHCID 1140TolueneSolvent

Procedure

To a solution of methyl p-cyano-trans-cinnamate (13.6 g, 73 mmol) in toluene (485 mL) was added 5% Pd/BaSO4 (2.7 g). After 9 hours under hydrogen gas at 4 bar (60 psi), the solution was filtered, concentrated in vacuo and chromatographed over silica gel, eluting with a step gradient of hexanes through 30% ethyl acetate/hexanes. The product containing fractions were combined and concentrated to give 10.6 g (77%) of colorless oil.

Workup

  1. filtrationthe solution was filtered
  2. concentrationconcentrated in vacuo
  3. customchromatographed over silica gel
  4. washeluting with a step gradient of hexanes through 30% ethyl acetate/hexanes
  5. additionThe product containing fractions
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-6423112fc5f740f1b81f8bc3b9883d73
Source dataset
uspto-grants-1998_03
Patent number
US05726159

Reaction notes

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