4-(Pyridin-2-yloxy)benzoic acid → Benzyl 3-oxo-3-[4-(pyridin-2-yloxy)phenyl]propanoate

HRID 1610594Notes

Reaction equation

HRID 1610594 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[O:7][C:8]1[CH:16]=[CH:15][C:11]([C:12]([OH:14])=O)=[CH:10][CH:9]=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:2]2[CH:3]=[CH:4][CH:5]=[CH:6][N:1]=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 222620524-(Pyridin-2-yloxy)benzoic acidHCID 178525630HCID 178525630, compound

Product 1

HCID 22262272Benzyl 3-oxo-3-[4-(pyridin-2-yloxy)phenyl]propanoate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To 4-(pyridin-2-yloxy)benzoic acid (20 g, 92.9 mmol) in tetrahydrofuran (300 ml) was added N,N′-carbonyldiimidazole (16.6 g, 102 mmol), and the mixture was heated under reflux for 1 hr. After cooling the reaction solution to room temperature, monobenzyl malonate magnesium salt (21 g, 51.2 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=2:1) to give the objective substance (20.6 g, 64%).

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 1 hr
  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=2:1)
  7. customto give the objective substance (20.6 g, 64%)

Sources & evidence

ORD record
ord-d7a9edfa441646c6b6f219682558061a
Source dataset
uspto-grants-2006_01
Patent number
US06982348B2

Reaction notes

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