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

HRID 1944642Notes

Reaction equation

HRID 1944642 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-1ed70c81f5e24ef1be82c8d20190f252
Source dataset
uspto-grants-2013_03
Patent number
US08394859B2

Reaction notes

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