4-(Pyridin-3-yloxy)benzoic acid → Benzyl 3-oxo-3-[4-(pyridin-3-yloxy)phenyl]propanoate

HRID 1610602Notes

Reaction equation

HRID 1610602 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([O:7][C:8]2[CH:16]=[CH:15][C:11]([C:12]([OH:14])=O)=[CH:10][CH:9]=2)[CH:2]=1.[Mg+].[C:18]([O:24][CH2:25][C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)(=[O:23])[CH2:19]C([O-])=O>O1CCCC1>[O:14]=[C:12]([C:11]1[CH:10]=[CH:9][C:8]([O:7][C:3]2[CH:2]=[N:1][CH:6]=[CH:5][CH:4]=2)=[CH:16][CH:15]=1)[CH2:19][C:18]([O:24][CH2:25][C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)=[O:23]

Participants

4

Reactant 2

HCID 222616674-(Pyridin-3-yloxy)benzoic acidHCID 178525630HCID 178525630, compound

Product 1

HCID 22261704Benzyl 3-oxo-3-[4-(pyridin-3-yloxy)phenyl]propanoate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 4-(pyridin-3-yloxy)benzoic acid (11.2 g, 52.0 mmol) in tetrahydrofuran (160 ml) was added N,N′-carbonyldiimidazole (9.28 g, 57.3 mmol), and the mixture was heated under reflux for 3 hrs. After cooling the reaction solution to room temperature, monobenzyl malonate magnesium salt (11.7 g, 28.6 mmol) was added, and the mixture was heated under reflux for 2 hrs. The reaction solution was concentrated and the residue was purified by silica gel column chromatography (hexane:ethyl acetate=1:1) to give the objective substance (14.1 g, 78%).

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 3 hrs
  3. temperaturethe mixture was heated
  4. temperatureunder reflux for 2 hrs
  5. concentrationThe reaction solution was concentrated
  6. customthe residue was purified by silica gel column chromatography (hexane:ethyl acetate=1:1)
  7. customto give the objective substance (14.1 g, 78%)

Sources & evidence

ORD record
ord-908103e8e15b438b848263bfe2f7cd85
Source dataset
uspto-grants-2006_01
Patent number
US06982348B2

Reaction notes

Loading…