1,5-Bis(4-methoxyphenyl)-1,4-pentadien-3-one → HCID 2801509, compound

HRID 1378396Notes

Reaction equation

HRID 1378396 reaction equation
[CH3:1][O:2][C:3]1[CH:22]=[CH:21][C:6]([CH:7]=[CH:8][C:9]([CH:11]=[CH:12][C:13]2[CH:18]=[CH:17][C:16]([O:19][CH3:20])=[CH:15][CH:14]=2)=[O:10])=[CH:5][CH:4]=1.[H][H]>C1COCC1.CO.[Pt](=O)=O>[CH3:20][O:19][C:16]1[CH:15]=[CH:14][C:13]([CH2:12][CH2:11][C:9](=[O:10])[CH2:8][CH2:7][C:6]2[CH:21]=[CH:22][C:3]([O:2][CH3:1])=[CH:4][CH:5]=2)=[CH:18][CH:17]=1

Participants

5

Reactant 2

HCID 1012201,5-Bis(4-methoxyphenyl)-1,4-pentadien-3-oneHCID 178418361HCID 178418361, compound

Product 1

HCID 2801509HCID 2801509, compoundYield 59.5%

Reagents, catalysts & solvents 2

HCID 345198Adams' catalystCatalystHCID 21899815MeOH tetrahydrofuranSolvent

Procedure

To a solution of commercially available di(4-methoxybenzylidene) acetone (3.5 g, 12 mmol) in THF-MeOH (1:1,100 mL) was added platinum (IV) oxide (90 mg) and the resulting mixture was stirred at room temperature under 4 atmospheres of hydrogen for 19 hours. The catalyst was filtered and washed with THF, and the filtrate was concentrated in vacuo. The residue was purified by chromatography on silica gel (hexane-ethyl acetate 3:1) to provide 1,5-bis(4-methoxyphenyl)-3-pentanone (2.13 g) and the reduced side product 1,5-bis(4-methoxyphenyl)-3-pentanol (1.0 g).

Workup

  1. filtrationThe catalyst was filtered
  2. washwashed with THF
  3. concentrationthe filtrate was concentrated in vacuo
  4. customThe residue was purified by chromatography on silica gel (hexane-ethyl acetate 3:1)

Sources & evidence

ORD record
ord-05fb986b373f45938dbf6fad166d9702
Source dataset
uspto-grants-1997_09
Patent number
US05668146

Reaction notes

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