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Water → Ethyl 2,6-Diisopropyl-4-(4-fluorophenyl)-3-hydroxymethylpyridine-5-carboxylate

HRID 973661
Notes
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Reaction equation

HRID 973661 reaction equation
[CH:1]([C:4]1[C:9]([C:10](OCC)=[O:11])=[C:8]([C:15]2[CH:20]=[CH:19][C:18]([F:21])=[CH:17][CH:16]=2)[C:7]([C:22]([O:24][CH2:25][CH3:26])=[O:23])=[C:6]([CH:27]([CH3:29])[CH3:28])[N:5]=1)([CH3:3])[CH3:2].O>C1(C)C=CC=CC=1.O1CCCC1>[CH:27]([C:6]1[C:7]([C:22]([O:24][CH2:25][CH3:26])=[O:23])=[C:8]([C:15]2[CH:16]=[CH:17][C:18]([F:21])=[CH:19][CH:20]=2)[C:9]([CH2:10][OH:11])=[C:4]([CH:1]([CH3:2])[CH3:3])[N:5]=1)([CH3:29])[CH3:28]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 2

HCID 962WaterHCID 10179180Diethyl 2,6-diisopropyl-4-(4-fluorophenyl)-pyridine-3,5-dicarboxylate

Product 1

HCID 10291957Ethyl 2,6-Diisopropyl-4-(4-fluorophenyl)-3-hydroxymethylpyridine-5-carboxylate

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 8028TetrahydrofuranSolvent

Procedure

21 ml (80.5 mmol) of a 3.5 molar solution of sodium bis-(2-methoxy ethoxy)-dihydroaluminate in toluene are added at -10° C. to -5° C. under nitrogen to a solution of 9.2 g (23 mmol) of the compound from Example III in 100 ml of dry tetrahydrofuran and the mixture is stirred at room temperature for 5 h. After cooling to 0° C., 100 ml of water are cautiously added dropwise and the mixture is extracted 3 times with 100 ml of ethyl acetate each time. The combined organic phases are washed with saturated sodium chloride solution, dried over magnesium sulphate and concentrated in vacuo. The residue is chromatographed on a column (200 g of silica gel 70-230 mesh, φ 4.5 cm, using ethyl acetate/petroleum ether 3:7).

Workup

  1. temperatureAfter cooling to 0° C.
  2. extractionthe mixture is extracted 3 times with 100 ml of ethyl acetate each time
  3. washThe combined organic phases are washed with saturated sodium chloride solution
  4. dry with materialdried over magnesium sulphate
  5. concentrationconcentrated in vacuo
  6. customThe residue is chromatographed on a column (200 g of silica gel 70-230 mesh, φ 4.5 cm, using ethyl acetate/petroleum ether 3:7)

Sources & evidence

ORD record
ord-09f4e6a165cb42daa081b92a00781317
Source dataset
uspto-grants-1991_11
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05064841

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes