[1-(3-Oxobut-1-en-1-yl)cyclopropyl]acetonitrile → [1-(3-Oxobutan-1-yl)cyclopropyl]acetonitrile

HRID 1683981Notes

Reaction equation

HRID 1683981 reaction equation
[O:1]=[C:2]([CH3:11])[CH:3]=[CH:4][C:5]1([CH2:8][C:9]#[N:10])[CH2:7][CH2:6]1.[H][H]>C(OCC)(=O)C.[Pd]>[O:1]=[C:2]([CH3:11])[CH2:3][CH2:4][C:5]1([CH2:8][C:9]#[N:10])[CH2:7][CH2:6]1

Participants

5

Reactant 2

HCID 53970073[1-(3-Oxobut-1-en-1-yl)cyclopropyl]acetonitrileHCID 178418361HCID 178418361, compound

Product 1

HCID 19041667[1-(3-Oxobutan-1-yl)cyclopropyl]acetonitrileYield 101.2%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

A solution of the olefin from Step 1 (4.08 g, 26.8 mmol) in 85 mL ethyl acetate was treated with 30 psi hydrogen over 5% palladium on carbon (300 rag) in a Parr shaker for 1.5 h. The mixture was filtered through celite and evaporated to give 4.1 g of the title compound.

Workup

  1. filtrationThe mixture was filtered through celite
  2. customevaporated

Sources & evidence

ORD record
ord-2694639149ec464c8d04aacd39c273a7
Source dataset
uspto-grants-1997_06
Patent number
US05639780

Reaction notes

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