4-(2-Ethoxycarbonyl-4-methyl-3-oxo-pent-1-enyl)benzoic acid → 4-(2-Ethoxycarbonyl-4-methyl-3-oxo-pentyl)benzoic acid

HRID 1162856Notes

Reaction equation

HRID 1162856 reaction equation
[CH2:1]([O:3][C:4]([C:6]([C:17](=[O:21])[CH:18]([CH3:20])[CH3:19])=[CH:7][C:8]1[CH:16]=[CH:15][C:11]([C:12]([OH:14])=[O:13])=[CH:10][CH:9]=1)=[O:5])[CH3:2]>C1COCC1.[Pd].ClCCl>[CH2:1]([O:3][C:4]([CH:6]([C:17](=[O:21])[CH:18]([CH3:20])[CH3:19])[CH2:7][C:8]1[CH:16]=[CH:15][C:11]([C:12]([OH:14])=[O:13])=[CH:10][CH:9]=1)=[O:5])[CH3:2]

Participants

5

Reactant 1

HCID 671199894-(2-Ethoxycarbonyl-4-methyl-3-oxo-pent-1-enyl)benzoic acid

Product 1

HCID 589520034-(2-Ethoxycarbonyl-4-methyl-3-oxo-pentyl)benzoic acidYield 89.4%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Procedure

50 g of 4-(2-ethoxycarbonyl-4-methyl-3-oxo-pent-1-enyl)benzoic acid are dissolved in 300 ml of THF, 1.00 g of palladium on carbon (10%) is added, and the mixture is hydrogenated under a hydrogen pressure of 4 bar in an autoclave for 24 h. The mixture is diluted with dichloromethane and filtered with suction through Celite, the residue is washed with dichloromethane and concentrated in vacuo. The residue is purified by chromatography on silica gel (ethyl acetate/n-heptane=3/1). 45 g of compound 45 are obtained as an oil. C16H20O5 (292.3) MS (ESI+): 293.1 (M+H)+, tR=1.37 min (Gradient 2).

Workup

  1. customfor 24 h
  2. filtrationfiltered with suction through Celite
  3. washthe residue is washed with dichloromethane
  4. concentrationconcentrated in vacuo
  5. customThe residue is purified by chromatography on silica gel (ethyl acetate/n-heptane=3/1)

Sources & evidence

ORD record
ord-7cb7c9baab26496ab562ea927af03da8
Source dataset
uspto-grants-2010_10
Patent number
US07820804B2

Reaction notes

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