Water → 1-Butanol,4-(imidazo[1,2-a]pyridin-5-yloxy)-

HRID 357008Notes

Reaction equation

HRID 357008 reaction equation
[H-].[Na+].Cl.Cl[C:5]1[N:10]2[CH:11]=[CH:12][N:13]=[C:9]2[CH:8]=[CH:7][CH:6]=1.[OH:14][CH2:15][CH2:16][CH2:17][CH2:18][O:19][Si](C(C)(C)C)(C)C.O>CS(C)=O>[OH:14][CH2:15][CH2:16][CH2:17][CH2:18][O:19][C:5]1[N:10]2[CH:11]=[CH:12][N:13]=[C:9]2[CH:8]=[CH:7][CH:6]=1

Participants

6

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 1864034-(Dimethyl-tert-butylsilyl)oxybutan-1-olHCID 219941745-Chloroimidazo[1,2-a]pyridine hydrochloride

Product 1

HCID 189368131-Butanol,4-(imidazo[1,2-a]pyridin-5-yloxy)-

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

In a nitrogen stream, 8.0 g (200 mmol) of 60% oily sodium hydride was added to a solution of 18.90 g (100 mmol) of 5-chloroimidazo[1,2-a]pyridine hydrochloride in 200 ml of dimethyl sulfoxide at 0° C., followed by stirring for 15 minutes. To this mixture, 20.44 g (100 mmol) of 4-hydroxy-1-t-butyldimethylsiloxybutane was added, followed by stirring room temperature for 5 hours. The reaction mixture was poured into water and extracted with ethyl acetate. The organic layer was washed with water and dried, after which the solvent was distilled off. The residue was purified by column chromatography (eluent: ethyl acetate) to yield 3.73 g (11.6%, orange oily substance) of the desired product.

Workup

  1. stirringby stirring room temperature for 5 hours
  2. extractionextracted with ethyl acetate
  3. washThe organic layer was washed with water
  4. customdried
  5. distillationafter which the solvent was distilled off
  6. customThe residue was purified by column chromatography (eluent: ethyl acetate)

Sources & evidence

ORD record
ord-3dc2156c8ccc40a8a198198e69ef81ad
Source dataset
uspto-grants-1998_11
Patent number
US05840732

Reaction notes

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