Reaction #2146694

Reaction equation

2-[4′-(3″-fluoropropoxy)phenyl]-6-methoxymethoxyimidazo[1,2-a]pyridine

hydrochloric acid

water

→

2-[4′-(3″-fluoropropoxy)phenyl]-6-hydroxyimidazo[1,2-a]pyridine

Yield 47.1%

Solvents

isopropyl alcohol

Conditions

Workup

1. 1
   TemperatureThen, the mixture was refluxed for 23 hours
2. 2
   TemperatureAfter the reaction solution was cooled
3. 3
   Extractionextracted twice by a salting-out extraction procedure
4. 4
   workup.ADDITIONwith addition of sodium chloride
5. 5
   DryingThe combined chloroform layer was dried over anhydrous magnesium sulfate
6. 6
   OtherThe resulting crude product was purified by silica gel column chromatography (elution solvent: chloroform/methanol=10/1)

Procedure

1.18 g (corresponding to 3.57 mmol) of 2-[4′-(3″-fluoropropoxy)phenyl]-6-methoxymethoxyimidazo[1,2-a]pyridine was dissolved in 29 mL of isopropyl alcohol, and 0.59 mL of conc. hydrochloric acid was added thereto. Then, the mixture was refluxed for 23 hours. After the reaction solution was cooled, the solution was poured into water, and extracted twice by a salting-out extraction procedure using chloroform with addition of sodium chloride. The combined chloroform layer was dried over anhydrous magnesium sulfate. The resulting crude product was purified by silica gel column chromatography (elution solvent: chloroform/methanol=10/1), to obtain 481 mg (corresponding to 1.68 mmol) of 2-[4′-(3″-fluoropropoxy)phenyl]-6-hydroxyimidazo[1,2-a]pyridine (hereinafter referred to as Compound 2) (FIG. 3, Step 10).

Source