5-(Benzyloxy)-2-tert-butylpyridine → 6-Tert-butylpyridin-3-ol

HRID 63278Notes

Reaction equation

HRID 63278 reaction equation
[CH3:1][C:2]([C:5]1[CH:10]=[CH:9][C:8]([O:11]CC2C=CC=CC=2)=[CH:7][N:6]=1)([CH3:4])[CH3:3]>C(O)C.[OH-].[OH-].[Pd+2]>[CH3:4][C:2]([C:5]1[N:6]=[CH:7][C:8]([OH:11])=[CH:9][CH:10]=1)([CH3:1])[CH3:3]

Participants

4

Reactant 1

HCID 207095055-(Benzyloxy)-2-tert-butylpyridine

Product 1

HCID 229582676-Tert-butylpyridin-3-ol

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 702EthanolSolvent

Procedure

To a stirred solution of 2-(1,1-dimethylethyl)-5-[(phenylmethyl)oxy]pyridine, (5.3 g) in ethanol (150 ml) was added 20% Pd(OH)2 (12.3 g) at 25-30 C. The above mixture was purged with hydrogen for 3 h until it had gone to completion by tlc. The reaction mixture was filtered through celite and the filtrate concentrated in vacuo and purified to give the title compound, 3.9 g

Workup

  1. customThe above mixture was purged with hydrogen for 3 h until it
  2. filtrationThe reaction mixture was filtered through celite
  3. concentrationthe filtrate concentrated in vacuo
  4. custompurified

Sources & evidence

ORD record
ord-25c309b0913641e2a7acc15eab8c2660
Source dataset
uspto-grants-2016_09
Patent number
US09447074B2

Reaction notes

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