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

HRID 8385

Reaction equation

HRID 8385 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

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 887MethanolSolventHCID 6344DichloromethaneSolvent

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-adab4b87712c4dafbdcd55a8abd05d2f
Source dataset
uspto-grants-2006_08
Patent number
US07087757B2

Linked notes

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