HCID 19965663, compound → HCID 19965659, compound

HRID 977275Notes

Reaction equation

HRID 977275 reaction equation
[O:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6]1[O:7][C:8]([CH3:25])=[C:9](/[CH:11]=[CH:12]/[C:13]2[CH:18]=[CH:17][C:16](/[CH:19]=[CH:20]/[CH:21]=[CH:22]/[CH:23]=[O:24])=[CH:15][CH:14]=2)[N:10]=1>[C].[Pd].C(OCC)(=O)C>[O:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6]1[O:7][C:8]([CH3:25])=[C:9]([CH2:11][CH2:12][C:13]2[CH:14]=[CH:15][C:16]([CH2:19][CH2:20][CH2:21][CH2:22][CH:23]=[O:24])=[CH:17][CH:18]=2)[N:10]=1

Participants

4

Reactant 1

HCID 19965663HCID 19965663, compound

Product 1

HCID 19965659HCID 19965659, compoundYield 92%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of (E,E,E)-5-[4-[2-[2-(2-furyl)-5-methyl-4-oxazolyl]vinyl]phenyl]-2,4-pentadien-1-al (2.4 g), palladium-carbon (5%, 0.3 g) and ethyl acetate (100 ml) was subjected to catalytic hydrogenation at 1 atm and room temperature. After the catalyst was filtered off, the filtrate was concentrated under reduced pressure. The residue was subjected to silica gel chromatography to yield 5-[4-[2-[2-(2-furyl)-5-methyl-4-oxazolyl]ethyl]phenyl]pentan-1-al (2.2 g, 92%) as an oily substance from the fraction eluted with ethyl acetate-hexane (1:1, v/v).

Workup

  1. customwas subjected to catalytic hydrogenation at 1 atm and room temperature
  2. filtrationAfter the catalyst was filtered off
  3. concentrationthe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-096bb28c6a4249b9a3656a71f8a84fc6
Source dataset
uspto-grants-1997_03
Patent number
US05614544

Reaction notes

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