Water → HCID 4678178, compound
Reaction equation
[BH4-].[Na+].[Cl:3][C:4]1[N:5]=[C:6]2[CH:11]=[CH:10][CH:9]=[CH:8][N:7]2[C:12]=1[CH:13]=[O:14].O>CCO>[Cl:3][C:4]1[N:5]=[C:6]2[CH:11]=[CH:10][CH:9]=[CH:8][N:7]2[C:12]=1[CH2:13][OH:14]Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
NaBH4 (1.52 g, 41.33 mmol, 1.5 eq) is added to a solution of 2-chloroimidazo[1,2-a]pyridine-3-carbaldehyde x173 (4.96 g, 27.56 mmol, 1 eq) in EtOH (100 ml). After 1 hour at room temperature, water (100 ml) is added and the aqueous layer is extracted with CH2Cl2 (3×50 ml). The combined organic layers are dried on anhydrous MgSO4, filtered and evaporated under reduced pressure. The resulting white solid is recrystallized in CH2Cl2/hexane to yield 3.9 g of (2-chloroimidazo[1,2-a]pyridin-3-yl)methanol x174.
Workup
- extractionthe aqueous layer is extracted with CH2Cl2 (3×50 ml)
- dry with materialThe combined organic layers are dried on anhydrous MgSO4
- filtrationfiltered
- customevaporated under reduced pressure
- customThe resulting white solid is recrystallized in CH2Cl2/hexane
Sources & evidence
- ORD record
- ord-1ffe22602c8444bfa6b5c4b5a3ef7aa7
- Source dataset
- uspto-grants-2012_05
- Patent number
- US08178533B2
Reaction notes
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