HCID 15596441, compound → HCID 23049317, compound

HRID 1722222Notes

Reaction equation

HRID 1722222 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]>CO.[Pd]>[CH2:1]([NH:5][C:6](=[O:19])/[CH:7]=[CH:8]/[CH2:9][CH2:10][CH2:11][CH2:12][C:13]1[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=1)[CH:2]([CH3:4])[CH3:3]

Participants

4

Reactant 1

HCID 15596441HCID 15596441, compound

Product 1

HCID 23049317HCID 23049317, compoundYield 66.9%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent2×

Procedure

The product of Example 1 (100 mg) was dissolved in dry methanol (3 ml), 5% Pd/C (25 mg) was added, and the mixture was hydrogenated at atmospheric pressure and room temperature. The reaction mixture was diluted with methanol and filtered. The solvent was removed in vacuo, and ether was added then removed in a stream of nitrogen. The last traces of solvent were removed in vacuo to yield N-isobutyl-7-phenylhept-2E-enamide (68 mg). Refractive index 1.39.

Workup

  1. customwas hydrogenated at atmospheric pressure and room temperature
  2. filtrationfiltered
  3. customThe solvent was removed in vacuo, and ether
  4. additionwas added
  5. customthen removed in a stream of nitrogen
  6. customThe last traces of solvent were removed in vacuo

Sources & evidence

ORD record
ord-caecd46a60814f039a83054c58002e04
Source dataset
uspto-grants-1989_08
Patent number
US04855086

Reaction notes

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