HCID 12743485, compound → HCID 12743495, compound

HRID 1937774Notes

Reaction equation

HRID 1937774 reaction equation
[C:1]([C:9]1[CH:14]=[C:13]([O:15][CH3:16])[CH:12]=[CH:11][C:10]=1[CH2:17][C:18]([OH:20])=[O:19])(=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>C(O)(=O)C.[Pd]>[CH2:1]([C:9]1[CH:14]=[C:13]([O:15][CH3:16])[CH:12]=[CH:11][C:10]=1[CH2:17][C:18]([OH:20])=[O:19])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 1

HCID 12743485HCID 12743485, compound

Product 1

HCID 12743495HCID 12743495, compoundYield 82.6%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 176Acetic AcidSolvent

Procedure

A solution of 2-benzoyl-4-methoxyphenylacetic acid (5.18 g, 20.3 mmol), prepared by the method of J. Med. Chem. 1981, 24, 998, in glacial acetic acid (200 mL) was treated under argon with 10% Pd/C (1 g) and hydrogenated at 50 psi for 17 h. The mixture was filtered using celite and the filtrate concentrated and chased with toluene and methylene chloride to give the title compound (4.3 g). 1H-NMR (350 MHz, CDCl3): δ 3.52 (s, 2H), 3.75 (s, 3H), 4.0 (s, 2H), 6.7 (m, 2H). 7.15 (m, 6H).

Workup

  1. filtrationThe mixture was filtered
  2. concentrationthe filtrate concentrated and chased with toluene and methylene chloride

Sources & evidence

ORD record
ord-0036212c331b4da484951bf1ba402751
Source dataset
uspto-grants-2002_05
Patent number
US06395919B1

Reaction notes

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