Water → HCID 22344568, compound

HRID 1070051Notes

Reaction equation

HRID 1070051 reaction equation
[BH4-].[Na+].[Cl:3][C:4]1[N:9]2[CH:10]=[C:11]([CH2:13][O:14][C:15]3[CH:22]=[CH:21][C:18]([CH:19]=[O:20])=[CH:17][CH:16]=3)[N:12]=[C:8]2[CH:7]=[CH:6][CH:5]=1.O1CCCC1.O>CO>[Cl:3][C:4]1[N:9]2[CH:10]=[C:11]([CH2:13][O:14][C:15]3[CH:16]=[CH:17][C:18]([CH2:19][OH:20])=[CH:21][CH:22]=3)[N:12]=[C:8]2[CH:7]=[CH:6][CH:5]=1

Participants

6

Reactant 4

HCID 962WaterHCID 8028TetrahydrofuranHCID 4311764Sodium borohydrideHCID 22344627HCID 22344627, compound

Product 1

HCID 22344568HCID 22344568, compoundYield 66%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Sodium borohydride (232 mg) was added to a solution of 4-(5-chloroimidazo[1,2-a]pyridin-2-ylmethoxy)benzaldehyde (3.52 g) in methanol (10 ml)-tetrahydrofuran (50 ml) at 0° C. After stirring for 1 hour, water was added to the reaction mixture and extracted with ethyl acetate. The ethyl acetate layer was washed with an aqueous saturated solution of sodium chloride, dried (MgSO4) and concentrated. The remaining crystals were recrystallized from ethyl acetate to obtain 4(5-chloroimidazo[1,2-a]pyridin-2-ylmethoxy)benzylalcohol (2.34 g, yield 66%) as colorless crystals. m.p. 169-171° C.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe ethyl acetate layer was washed with an aqueous saturated solution of sodium chloride
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated
  5. customThe remaining crystals were recrystallized from ethyl acetate

Sources & evidence

ORD record
ord-87c75c02c7324261a5a6d08ac2000c63
Source dataset
uspto-grants-2001_06
Patent number
US06251926B1

Reaction notes

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