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Methanol → 4-Benzyl-5-bromo-2-(3-hydroxybutyl)pyridine

HRID 1359392
Notes
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Reaction equation

HRID 1359392 reaction equation
[CH2:1]([C:8]1[C:13]([Br:14])=[CH:12][N:11]=[C:10]([C:15]#[C:16][CH:17]([OH:19])[CH3:18])[CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CO.O1CCCC1.[H][H]>[Pt](=O)=O.C(OCC)(=O)C>[CH2:1]([C:8]1[C:13]([Br:14])=[CH:12][N:11]=[C:10]([CH2:15][CH2:16][CH:17]([OH:19])[CH3:18])[CH:9]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 887MethanolHCID 8028TetrahydrofuranHCID 181823824-Benzyl-5-bromo-2-(3-hydroxy-1-butynyl)pyridineHCID 178418361HCID 178418361, compound

Product 1

HCID 181823054-Benzyl-5-bromo-2-(3-hydroxybutyl)pyridineYield 24.7%

Reagents, catalysts & solvents 2

HCID 345198
Adams' catalyst
Catalyst
HCID 8857Ethyl AcetateSolvent

Procedure

200 mg of 4-benzyl-5-bromo-2-(3-hydroxy-1-butynyl)pyridine (Example 189a) and 10 mg of platinum (IV) oxide were added to 10 ml of methanol, 10 ml of tetrahydrofuran and 10 ml of ethyl acetate, followed by stirring at room temperature at normal pressure in a hydrogen atmosphere overnight. The catalyst was filtered off and the filtrate was evaporated, to give 50 mg of the target compound.

Workup

  1. filtrationThe catalyst was filtered off
  2. customthe filtrate was evaporated

Sources & evidence

ORD record
ord-bf2548f2efcf47109982c15ea99c920d
Source dataset
uspto-grants-2003_07
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06599917B1

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes