HCID 53811135, compound → HCID 15596444, compound

HRID 1722221Notes

Reaction equation

HRID 1722221 reaction equation
[CH2:1]([NH:5][C:6](=[O:19])[CH:7]=[CH:8][CH2:9][CH2:10][C:11]#[C:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)[CH:2]([CH3:4])[CH3:3].[H][H]>CO.[Pd].[O-]S([O-])(=O)=O.[Ba+2]>[CH2:1]([NH:5][C:6](=[O:19])/[CH:7]=[CH:8]/[CH2:9][CH2:10]/[CH:11]=[CH:12]\[C:13]1[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=1)[CH:2]([CH3:4])[CH3:3]

Participants

5

Reactant 2

HCID 53811135HCID 53811135, compoundHCID 178418361HCID 178418361, compound2×

Product 1

HCID 15596444HCID 15596444, compoundYield 60.5%

Reagents, catalysts & solvents 2

HCID 16218511Pd barium sulfateCatalystHCID 887MethanolSolvent2×

Procedure

N-Isobutyl-7-phenylhept-2-en-6-ynamide (100 mg) and 5% Pd/BaSO4 (17 ml) in dry methanol (3 ml) at 20° C. was treated with hydrogen until hydrogen uptake was 85% of theoretical. The mixture was diluted with methanol, filtered and the solvent was removed from the filtrate. The residue was treated with ether and the solvent removed in a stream of nitrogen. The product was purified by chromatography on silica (15 g), eluting with 1:1 ether:hexane grading to 100% ether to give N-isobutyl-7-phenylhepta-2E,6Z-dienamide (61 mg) as a yellow oil which crystallised on standing mp 42°-5° C.

Workup

  1. filtrationfiltered
  2. customthe solvent was removed from the filtrate
  3. additionThe residue was treated with ether
  4. customthe solvent removed in a stream of nitrogen
  5. customThe product was purified by chromatography on silica (15 g)
  6. washeluting with 1:1 ether

Sources & evidence

ORD record
ord-ca29492cc6f241f48fd41039c8b5ce0e
Source dataset
uspto-grants-1989_08
Patent number
US04855086

Reaction notes

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