Sodium cyanoborohydride → HCID 18182353, compound

HRID 1359308Notes

Reaction equation

HRID 1359308 reaction equation
[CH3:1][O:2][C:3]1[C:8]([CH:9]([C:11]2[S:12][CH:13]=[CH:14][CH:15]=2)O)=[CH:7][CH:6]=[CH:5][N:4]=1.C([BH3-])#N.[Na+]>[I-].[Zn+2].[I-].ClCCCl>[CH3:1][O:2][C:3]1[C:8]([CH2:9][C:11]2[S:12][CH:13]=[CH:14][CH:15]=2)=[CH:7][CH:6]=[CH:5][N:4]=1

Participants

5

Reactant 2

HCID 5003444Sodium cyanoborohydrideHCID 181824832-Methoxy-α-2-thienyl-3-pyridinemethanol

Product 1

HCID 18182353HCID 18182353, compoundYield 53.8%

Reagents, catalysts & solvents 2

HCID 9883512zinc(II)iodideCatalystHCID 111,2-DichloroethaneSolvent

Procedure

A mixture of 1.47 g of 2-methoxy-3-[2-thienyl(hydroxy)methyl]pyridine, 3.2 g of zinc iodide, 3.4 g of sodium cyanoborohydride and 30 ml of 1,2-dichloroethane was stirred at room temperature for two nights. Insoluble matters were filtered off, and to the filtrate was added an aqueous sodium hydroxide solution. The mixture was extracted with ethyl acetate, and the organic phase was washed with brine and the solvent was evaporated. Then, the residue was subjected to silica gel column chromatography and eluted with hexane and then with hexane/ethyl acetate (40:1), to give 734 mg of the target compound.

Workup

  1. filtrationInsoluble matters were filtered off
  2. additionto the filtrate was added an aqueous sodium hydroxide solution
  3. extractionThe mixture was extracted with ethyl acetate
  4. washthe organic phase was washed with brine
  5. customthe solvent was evaporated
  6. washeluted with hexane

Sources & evidence

ORD record
ord-0c87f79b31474662801cde4dfece0887
Source dataset
uspto-grants-2003_07
Patent number
US06599917B1

Reaction notes

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