HCID 54315832, compound → HCID 23353794, compound

HRID 235200Notes

Reaction equation

HRID 235200 reaction equation
[CH2:1]([C:5]1[CH:27]=[CH:26][C:8]([CH:9]=[CH:10][C:11]([C:13]2[CH:18]=[CH:17][C:16]([CH2:19][CH2:20][CH2:21][C:22]([O:24][CH3:25])=[O:23])=[CH:15][CH:14]=2)=[O:12])=[CH:7][CH:6]=1)[CH2:2][CH2:3][CH3:4]>CO.[Pd]>[CH2:1]([C:5]1[CH:27]=[CH:26][C:8]([CH2:9][CH2:10][CH:11]([C:13]2[CH:14]=[CH:15][C:16]([CH2:19][CH2:20][CH2:21][C:22]([O:24][CH3:25])=[O:23])=[CH:17][CH:18]=2)[OH:12])=[CH:7][CH:6]=1)[CH2:2][CH2:3][CH3:4]

Participants

4

Reactant 1

HCID 54315832HCID 54315832, compound

Product 1

HCID 23353794HCID 23353794, compoundYield 97.6%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a solution of 4.40 g of methyl 4-[4-(4-butylcinnamoyl)phenyl]butyrate in 44 ml of methanol, 0.24 g of 10% palladium on carbon was added, and hydrogenation was carried out at an ordinary temperature and under ordinary pressure for 3.5 hours. After the catalyst was removed by filtration, 0.27 g of sodium borohydride was added to the filtrate under ice-cooling, and then stirring was continued at room temperature for 2 hours. After the reaction solvent was removed under reduced pressure, the residue was added with water and extracted with ether. The ether layer was washed with water, dried, and then the solvent was removed under reduced pressure to yield 4.34 g of colorless oil.

Workup

  1. customAfter the catalyst was removed by filtration, 0.27 g of sodium borohydride
  2. additionwas added to the filtrate under ice-
  3. temperaturecooling
  4. waitwas continued at room temperature for 2 hours
  5. customAfter the reaction solvent was removed under reduced pressure
  6. additionthe residue was added with water
  7. extractionextracted with ether
  8. washThe ether layer was washed with water
  9. customdried
  10. customthe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-1f343906b99e4252b84a6fa31e629873
Source dataset
uspto-grants-1997_01
Patent number
US05597848

Reaction notes

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