HCID 68649188, compound → HCID 68649141, compound

HRID 219560Notes

Reaction equation

HRID 219560 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][C:6]([CH:9]=[CH:10][C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])=[CH:5][C:4]=1[O:18][CH3:19])#[N:2].[H][H]>C(OCC)(=O)C.[Pd]>[C:1]([C:3]1[CH:8]=[CH:7][C:6]([CH2:9][CH2:10][C:11]([O:13][C:14]([CH3:15])([CH3:17])[CH3:16])=[O:12])=[CH:5][C:4]=1[O:18][CH3:19])#[N:2]

Participants

5

Reactant 2

HCID 68649188HCID 68649188, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 68649141HCID 68649141, compoundYield 99.2%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of tert-butyl 3-(4-cyano-3-methoxyphenyl)acrylate obtained in step 1 (3.5 g) in ethyl acetate (150 mL) was added palladium on carbon (500 mg) and the mixture was put under a pressure of 4 kg of hydrogen for 12 h at RT. The catalyst was removed by filtration and the solvents were removed under vacuum to afford the title compound as white solid (3.5 g, 97%). 1H-NMR (CDCl3, 400 MHz) δ 7.41-7.43 (1H, s), 6.80-6.83 (2H, m), 3.88 (3H, s), 2.89-2.93 (2H, t), 2.51-2.55 (2H, t), 1.34 (9H, s). LC/MS: 279.1 (M+H)+. HPLC (Method C) Rt 2.40 min (Purity: 99.7%).

Workup

  1. customThe catalyst was removed by filtration
  2. customthe solvents were removed under vacuum

Sources & evidence

ORD record
ord-da0d3081cc1847f8879f4b514dca579c
Source dataset
uspto-grants-2012_06
Patent number
US08202856B2

Reaction notes

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