Ethanol → Ethyl 2,6-diisopropyl-5-ethoxymethyl-4-(4-fluorophenyl)pyridine-3-carboxylate

HRID 1084895Notes

Reaction equation

HRID 1084895 reaction equation
[CH2:1]([OH:3])[CH3:2].[H-].[Na+].Cl[CH2:7][C:8]1[C:9]([C:25]2[CH:30]=[CH:29][C:28]([F:31])=[CH:27][CH:26]=2)=[C:10]([C:20]([O:22][CH2:23][CH3:24])=[O:21])[C:11]([CH:17]([CH3:19])[CH3:18])=[N:12][C:13]=1[CH:14]([CH3:16])[CH3:15]>O1CCCC1>[CH:17]([C:11]1[C:10]([C:20]([O:22][CH2:23][CH3:24])=[O:21])=[C:9]([C:25]2[CH:30]=[CH:29][C:28]([F:31])=[CH:27][CH:26]=2)[C:8]([CH2:7][O:3][CH2:1][CH3:2])=[C:13]([CH:14]([CH3:15])[CH3:16])[N:12]=1)([CH3:18])[CH3:19]

Participants

5

Reactant 3

HCID 702EthanolHCID 24758Sodium hydrideHCID 20081869Ethyl 5-chloromethyl-2,6-diisopropyl-4-(4-fluorophenyl)pyridine-3-carboxylate

Product 1

HCID 20081845Ethyl 2,6-diisopropyl-5-ethoxymethyl-4-(4-fluorophenyl)pyridine-3-carboxylate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

4.4 ml (76 mmol) of absolute ethanol are added dropwise at room temperature to a suspension of 2.29 g (76 mmol) of sodium hydride (80% strength) in 30 ml of absolute tetrahydrofuran and the mixture is stirred for 30 minutes. A solution of 2.7 g (7.6 mmol) of the compound from Example 86 are then added dropwise in 20 ml of absolute tetrahydrofuran and the mixture is heated overnight under reflux. The reaction batch is subsequently poured onto ice water and, after the pH has been adjusted to 8, extracted several times using ether. The organic phase is washed with sodium chloride solution, dried over sodium sulphate, concentrated and chromatographed over silica gel (eluent ethyl acetate/petroleum ether 5195).

Workup

  1. temperaturethe mixture is heated overnight
  2. temperatureunder reflux
  3. additionThe reaction batch is subsequently poured onto ice water
  4. extractionextracted several times
  5. washThe organic phase is washed with sodium chloride solution
  6. dry with materialdried over sodium sulphate
  7. concentrationconcentrated
  8. customchromatographed over silica gel (eluent ethyl acetate/petroleum ether 5195)

Sources & evidence

ORD record
ord-2fc3282d1f6f4c8ba184187b1dbca373
Source dataset
uspto-grants-1991_04
Patent number
US05006530

Reaction notes

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