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Epichlorohydrin → 2-[4-[(2,3-Epoxy)propoxy]phenyl]-8-methylimidazo[1,2-a]pyridine

HRID 1268693
Notes
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Reaction equation

HRID 1268693 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:9]=[C:10]3[C:15]([CH3:16])=[CH:14][CH:13]=[CH:12][N:11]3[CH:17]=2)=[CH:4][CH:3]=1.[OH-].[K+].[CH2:20]([CH:22]1[O:24][CH2:23]1)Cl>CO.ClCCl>[O:24]1[CH2:23][CH:22]1[CH2:20][O:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[N:9]=[C:10]3[C:15]([CH3:16])=[CH:14][CH:13]=[CH:12][N:11]3[CH:17]=2)=[CH:6][CH:7]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 3

HCID 7835EpichlorohydrinHCID 14797Potassium HydroxideHCID 220156592-[4-Hydroxyphenyl]-8-methylimidazo[1,2-a]pyridine

Product 1

HCID 220156322-[4-[(2,3-Epoxy)propoxy]phenyl]-8-methylimidazo[1,2-a]pyridine

Reagents, catalysts & solvents 2

HCID 887MethanolSolvent
HCID 6344
Dichloromethane
Solvent

Procedure

The product of Step B (27 g) in methanol (500 mL) was treated with potassium hydroxide (14 g) and stirred at ambient temperature for 2 hours. To this solution was then added epichlorohydrin (9.4 mL) and the mixture stirred for an additional 48 hours. The reaction mixture was diluted with dichloromethane, filtered and the filtrate washed with water, dried, sodium sulfate filtered and evaporated to afford the title compound (18.2 g).

Workup

  1. filtrationfiltered
  2. washthe filtrate washed with water
  3. customdried
  4. filtrationsodium sulfate filtered
  5. customevaporated

Sources & evidence

ORD record
ord-5338b8c739c84f7abf4fbff8f8758892
Source dataset
uspto-grants-2007_04
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07199117B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes