Methanol → 2-Hydroxymethyl-6-phenylpyridine

HRID 349973Notes

Reaction equation

HRID 349973 reaction equation
Cl[C:2]1[C:3]([CH2:14][OH:15])=[N:4][C:5]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)=[CH:6][CH:7]=1.C(N(CC)CC)C.CO>[C].[Pd].O1CCCC1>[C:8]1([C:5]2[N:4]=[C:3]([CH2:14][OH:15])[CH:2]=[CH:7][CH:6]=2)[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1

Participants

6

Reactant 3

HCID 887MethanolHCID 8471TriethylamineHCID 230249223-Chloro-6-phenyl-2-pyridylmethanol

Product 1

HCID 107261862-Hydroxymethyl-6-phenylpyridineYield 95%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 3-chloro-6-phenyl-2-pyridylmethanol (2.20 g), 5% palladium-carbon (1.10 g), triethylamine (1.4 ml), methanol (20 ml) and tetrahydrofuran (20 ml) was stirred at room temperature under a hydrogen atmosphere. After palladium-carbon was removed by filtration, the filtrate was concentrated. The residue was subjected to silica gel column chromatography to obtain 6-phenyl-2-pyridylmethanol (1.76 g, yield 95%) as a colorless oily substance from the fraction eluted with ethyl acetate-hexane (1:5, volume ratio).

Workup

  1. customAfter palladium-carbon was removed by filtration
  2. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-1d9201298fda49c3a5bdf04b07ebea9b
Source dataset
uspto-grants-2007_02
Patent number
US07179823B1

Reaction notes

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