5-Phenoxypyridine-2-carboxylic acid → Benzyl 3-oxo-3-(5-phenoxypyridin-2-yl)propanoate

HRID 1610586Notes

Reaction equation

HRID 1610586 reaction equation
[O:1]([C:8]1[CH:9]=[CH:10][C:11]([C:14]([OH:16])=O)=[N:12][CH:13]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=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:16]=[C:14]([C:11]1[CH:10]=[CH:9][C:8]([O:1][C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)=[CH:13][N:12]=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 222614835-Phenoxypyridine-2-carboxylic acidHCID 178525630HCID 178525630, compound

Product 1

HCID 22262297Benzyl 3-oxo-3-(5-phenoxypyridin-2-yl)propanoate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 5-phenoxypyridine-2-carboxylic acid (10 g, 46.5 mmol) in tetrahydrofuran (150 ml) was added N,N′-carbonyldiimidazole (8.29. g, 51.1 mmol), and the mixture was heated under reflux for 1 hr. After cooling the reaction solution to room temperature, monobenzyl malonate magnesium salt (10.5 g, 25.6 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=2:1) to give the objective substance (11.2 g, 76%).

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 (11.2 g, 76%)

Sources & evidence

ORD record
ord-7797921dc8ca4a38880024c4b3c1785f
Source dataset
uspto-grants-2006_01
Patent number
US06982348B2

Reaction notes

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