Methanol → 4-(2-Cyano-3-oxopentyl)benzonitrile

HRID 403500Notes

Reaction equation

HRID 403500 reaction equation
[C:1]([C:3]([C:13](=[O:16])[CH2:14][CH3:15])=[CH:4][C:5]1[CH:12]=[CH:11][C:8]([C:9]#[N:10])=[CH:7][CH:6]=1)#[N:2].CO.[H][H]>[Pd].CC#N>[C:1]([CH:3]([C:13](=[O:16])[CH2:14][CH3:15])[CH2:4][C:5]1[CH:12]=[CH:11][C:8]([C:9]#[N:10])=[CH:7][CH:6]=1)#[N:2]

Participants

6

Reactant 3

HCID 887MethanolHCID 683795824-(2-Cyano-3-oxopent-1-enyl)benzonitrileHCID 178418361HCID 178418361, compound2×

Product 1

HCID 683790834-(2-Cyano-3-oxopentyl)benzonitrileYield 99.1%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 6342AcetonitrileSolvent

Procedure

To a hydrogenation reactor was charged with 4-(2-cyano-3-oxopent-1-enyl)benzonitrile (24) (20 g, 95.1 mmol), Pd/C (2 g, 10%, wet), MeOH (100 ml) and MeCN (100 ml). The mixture was stirred at 25° C. under 50 psi hydrogen for 2 h until absorption of hydrogen was stopped. The mixture was filtered through a celite pad to remove catalyst. It was concentrated under reduced pressure to give product 25 (20 g, 99%) as an oil. The product was directly used for the next step reaction without further purification.

Workup

  1. filtrationThe mixture was filtered through a celite pad
  2. customto remove catalyst
  3. concentrationIt was concentrated under reduced pressure

Sources & evidence

ORD record
ord-54c40655392246019e60f21df6a81428
Source dataset
uspto-grants-2014_06
Patent number
US08748435B2

Reaction notes

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