Potassium Hydroxide → HCID 67946621, compound

HRID 1164825Notes

Reaction equation

HRID 1164825 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:13]([CH2:14][CH:15]=[CH:16][OH:17])=[C:12]([CH:18]([CH3:20])[CH3:19])[N:11]=[C:10]([CH:21]([CH3:23])[CH3:22])[C:9]=2[C:24]([O:26]C)=[O:25])=[CH:4][CH:3]=1.[OH-].[K+]>C(O)CCC>[F:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[C:13]([CH2:14][CH:15]=[CH:16][OH:17])=[C:12]([CH:18]([CH3:19])[CH3:20])[N:11]=[C:10]([CH:21]([CH3:22])[CH3:23])[C:9]=2[C:24]([OH:26])=[O:25])=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 14797Potassium HydroxideHCID 86743783HCID 86743783, compound

Product 1

HCID 67946621HCID 67946621, compoundYield 55.4%

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent2×

Procedure

A solution of 4-(4-Fluorophenyl)-5-(3-hydroxy-2-propenyl)-2,6-bis(1-methylethyl)-3-pyridinecarboxylic acid, methyl ester (7.5 g, 0.0202 mol) and KOH (3.66 g, 0.0652 mol) in n-butanol was refluxed for 72 hours followed by concentration of the butanol under reduced pressure. The residue was partitioned between water (250 ml) and diethylether (100 ml). The aqueous layer was acidified (citric acid) and extracted with chloroform (3×150 ml). The organic layer was dried (MgSO4) and concentrated to yield 4.0 g of the title compound.

Workup

  1. customThe residue was partitioned between water (250 ml) and diethylether (100 ml)
  2. extractionextracted with chloroform (3×150 ml)
  3. dry with materialThe organic layer was dried (MgSO4)
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-b1350a2f77e14bc08fafa7f388ac3f9f
Source dataset
uspto-grants-1990_03
Patent number
US04906624

Reaction notes

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