Water → Ethyl 2,6-diisopropyl-4-(4-fluorophenyl)-5-phenoxymethylpyridine-3-carboxylate

HRID 1681257Notes

Reaction equation

HRID 1681257 reaction equation
Cl[CH2:2][C:3]1[C:4]([C:20]2[CH:25]=[CH:24][C:23]([F:26])=[CH:22][CH:21]=2)=[C:5]([C:15]([O:17][CH2:18][CH3:19])=[O:16])[C:6]([CH:12]([CH3:14])[CH3:13])=[N:7][C:8]=1[CH:9]([CH3:11])[CH3:10].[O-:27][C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1.[Na+].O>O1CCCC1>[CH:12]([C:6]1[C:5]([C:15]([O:17][CH2:18][CH3:19])=[O:16])=[C:4]([C:20]2[CH:21]=[CH:22][C:23]([F:26])=[CH:24][CH:25]=2)[C:3]([CH2:2][O:27][C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)=[C:8]([CH:9]([CH3:10])[CH3:11])[N:7]=1)([CH3:13])[CH3:14]

Participants

5

Reactant 3

HCID 962WaterHCID 4445035Phenolate SodiumHCID 20081869Ethyl 5-chloromethyl-2,6-diisopropyl-4-(4-fluorophenyl)pyridine-3-carboxylate

Product 1

HCID 20081776Ethyl 2,6-diisopropyl-4-(4-fluorophenyl)-5-phenoxymethylpyridine-3-carboxylate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

3.22 g (9.1 mmol) of the compound from Example 86 dissolved in 50 ml of absolute tetrahydrofuran are added dropwise at 0° C. to a solution of 2.11 g (18.2 mmol) of sodium phenoxide in 50 ml of absolute tetrahydrofuran and the mixture is heated to reflux for 4 days. After cooling to room temperature, the mixture is diluted using 150 ml of water and extracted several times using ether. The combined organic phases are dried over magnesium sulphate and concentrated in vacuo, and the residue is chromatographed on a column (silica gel 70-230 mesh, using petroleum ether/ethyl acetate 95.5).

Workup

  1. temperaturethe mixture is heated
  2. temperatureto reflux for 4 days
  3. additionthe mixture is diluted
  4. extractionextracted several times
  5. dry with materialThe combined organic phases are dried over magnesium sulphate
  6. concentrationconcentrated in vacuo
  7. customthe residue is chromatographed on a column (silica gel 70-230 mesh, using petroleum ether/ethyl acetate 95.5)

Sources & evidence

ORD record
ord-51964dfc2c70491ab474bf43322cb53c
Source dataset
uspto-grants-1992_12
Patent number
US05169857

Reaction notes

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