HCID 23103640, compound → HCID 23103643, compound

HRID 2116484Notes

Reaction equation

HRID 2116484 reaction equation
[CH2:1]([C:3]1[CH:8]=[CH:7][C:6]([CH:9]([C:11]2[CH:16]=[CH:15][N:14]=[CH:13][C:12]=2[OH:17])O)=[CH:5][CH:4]=1)[CH3:2]>[Pd].C(O)(=O)C>[CH2:1]([C:3]1[CH:8]=[CH:7][C:6]([CH2:9][C:11]2[CH:16]=[CH:15][N:14]=[CH:13][C:12]=2[OH:17])=[CH:5][CH:4]=1)[CH3:2]

Participants

4

Reactant 1

HCID 23103640HCID 23103640, compound

Product 1

HCID 23103643HCID 23103643, compoundYield 40%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 176Acetic AcidSolvent

Procedure

Next, to a mixture of (4-ethylphenyl)-(3-hydroxypyridin-4-yl)-methanol (10.54 g, 46.0 mmol) and acetic acid (100 ml), 5% palladium/carbon (5.0 g) was added and stirred under a hydrogen atmosphere at room temperature for 7 hours. After filtration to remove the insoluble materials, the filtrate was concentrated under reduced pressure and the resulting residue was recrystallized (ethyl acetate) to give the titled compound (3.91 g, 40%) as a colorless powder. Moreover, the mother liquor was purified by NH silica gel column chromatography (chloroform:methanol=20:1) to give 4-(4-ethylbenzyl)-3-hydroxypyridine (4.55 g, 46%) as a light-brown powder.

Workup

  1. additionwas added
  2. filtrationAfter filtration
  3. customto remove the insoluble materials
  4. concentrationthe filtrate was concentrated under reduced pressure
  5. customthe resulting residue was recrystallized (ethyl acetate)

Sources & evidence

ORD record
ord-1bf123a11d6440c39ae6436454dcd890
Source dataset
uspto-grants-2008_10
Patent number
US07439232B2

Reaction notes

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