Iodoethane → HCID 22930062, compound

HRID 1295989Notes

Reaction equation

HRID 1295989 reaction equation
[CH3:1][C:2]1[C:7]([CH2:8][OH:9])=[CH:6][N:5]=[C:4]([CH3:10])[C:3]=1[OH:11].Cl.[H-].[Na+].[CH2:15](I)[CH3:16].C(=O)([O-])O.[Na+]>CN(C)C=O.C(OCC)(=O)C.O1CCCC1>[CH2:15]([O:11][C:3]1[C:2]([CH3:1])=[C:7]([CH2:8][OH:9])[CH:6]=[N:5][C:4]=1[CH3:10])[CH3:16]

Participants

7

Reactant 4

HCID 6340IodoethaneHCID 24758Sodium hydrideHCID 674174-Desoxypyridoxine hydrochlorideHCID 516892Sodium Bicarbonate

Product 1

HCID 22930062HCID 22930062, compoundYield 44%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolvent2×HCID 21939870Tetrahydrofuran ethyl acetateSolvent

Procedure

A suspension of 4-deoxypyridoxine hydrochloride (0.99 g, 5.2 mmol) in dimethylformamide (10 ml) was added dropwise to a suspension of 60% NaH (0.42 g, 10.5 mmol) in dimethylformamide (10 ml) while cooling on ice, and the mixture was stirred at room temperature for 1 day. Ethyl iodide (0.44 ml, 5.5 mmol) was then added dropwise at room temperature and stirring was continued for 17 hours. After confirming completion of the reaction by thin layer chromatography, the mixture was poured into semi-saturated aqueous sodium hydrogencarbonate and extraction was performed with ethyl acetate-tetrahydrofuran (1:1). The extract was washed with brine and dried over anhydrous magnesium sulfate, the solvent was distilled off under reduced pressure and the residue was purified by silica gel column chromatography (solvent: methylene chloride-methanol) to yield the title compound (0.415 g, 44%).

Workup

  1. temperaturewhile cooling on ice
  2. stirringstirring
  3. waitwas continued for 17 hours
  4. customcompletion of the reaction by thin layer chromatography
  5. washThe extract was washed with brine
  6. dry with materialdried over anhydrous magnesium sulfate
  7. distillationthe solvent was distilled off under reduced pressure
  8. customthe residue was purified by silica gel column chromatography (solvent: methylene chloride-methanol)

Sources & evidence

ORD record
ord-fede23d964424760b3a3f7c778d89cb1
Source dataset
uspto-grants-2007_07
Patent number
US07244730B2

Reaction notes

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