5-(2,3,4-Trimethoxyphenyl)-5-oxovaleric acid → 5-(2,3,4-Trimethoxyphenyl)pentanoic acid

HRID 33955Notes

Reaction equation

HRID 33955 reaction equation
O=[C:2]([C:9]1[CH:14]=[CH:13][C:12]([O:15][CH3:16])=[C:11]([O:17][CH3:18])[C:10]=1[O:19][CH3:20])[CH2:3][CH2:4][CH2:5][C:6]([OH:8])=[O:7]>C(O)C.[Pd]>[CH3:20][O:19][C:10]1[C:11]([O:17][CH3:18])=[C:12]([O:15][CH3:16])[CH:13]=[CH:14][C:9]=1[CH2:2][CH2:3][CH2:4][CH2:5][C:6]([OH:8])=[O:7]

Participants

4

Reactant 1

HCID 193481585-(2,3,4-Trimethoxyphenyl)-5-oxovaleric acid

Product 1

HCID 435890935-(2,3,4-Trimethoxyphenyl)pentanoic acidYield 97.74%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

5-Oxo-5-(2,3,4-trimethoxy-phenyl)-pentanoic acid (7.05 g 24.97 mmol) was dissolved in 100 mL of anhydrous ethanol under inert atmosphere and 2.0 g of Pd—C was added. The nitrogen gas was removed by vacuum, and hydrogen gas was passed into the flask. The reaction mixture was stirred for 1 h. The completion of the reaction was confirmed by TLC. The reaction mixture was filtered through celite. The solvent was evaporated under reduced pressure to obtain 6.48 g (97.74%) of 62 (colorless oil) which was pure by NMR.

Workup

  1. additionwas added
  2. customThe nitrogen gas was removed by vacuum, and hydrogen gas
  3. filtrationThe reaction mixture was filtered through celite
  4. customThe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-49a3d40815394918bb86530586be9444
Source dataset
uspto-grants-2008_09
Patent number
US07429681B2

Reaction notes

Loading…