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Sodium hydride → HCID 57422597, compound

HRID 2426775
Notes
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Reaction equation

HRID 2426775 reaction equation
[H-].[Na+].[Br:3][C:4]1[C:5]([CH3:11])=[CH:6][C:7]([OH:10])=[N:8][CH:9]=1.CC1C=CC(S(O[CH2:23][CH2:24][C:25]([OH:28])([CH3:27])[CH3:26])(=O)=O)=CC=1>CN(C=O)C>[Br:3][C:4]1[C:5]([CH3:11])=[CH:6][C:7]([O:10][CH2:23][CH2:24][C:25]([CH3:27])([OH:28])[CH3:26])=[N:8][CH:9]=1.[Br:3][C:4]1[C:5]([CH3:11])=[CH:6][C:7](=[O:10])[N:8]([CH2:23][CH2:24][C:25]([OH:28])([CH3:27])[CH3:26])[CH:9]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 3

HCID 24758Sodium hydrideHCID 140012952-Methyl-4-[(4-methylbenzenesulfonyl)oxy]butan-2-olHCID 178429280HCID 178429280, compound

Product 2

HCID 57422597HCID 57422597, compoundHCID 574225985-bromo-1-(3-hydroxy-3-methylbutyl)-4-methylpyridin-2(1H)-one

Reagents, catalysts & solvents 1

HCID 6228
Dimethylformamide
Solvent

Procedure

In an atmosphere of nitrogen, sodium hydride was added under ice-cooling to a mixture of 5-bromo-4-methylpyridin-2-ol and DMF, followed by stirring at room temperature for 1 hour. Then, 3-hydroxy-3-methylbutyl 4-methylbenzenesulfonate was added thereto, followed by stirring at 40° C. for 14 hours to obtain 4-[(5-bromo-4-methylpyridin-2-yl)oxy]2-methylbutan-2-ol and 5-bromo-1-(3-hydroxy-3-methylbutyl)-4-methylpyridin-2(1H)-one.

Workup

  1. stirringby stirring at 40° C. for 14 hours

Sources & evidence

ORD record
ord-c2916366ee204a46a7cc614a309bdfab
Source dataset
uspto-grants-2011_06
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07968552B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes