Sodium Chloride → 3-[p-(3-Acetoxy-1-hydroxy-2-methylpropyl)benzyl]pyridine

HRID 986448Notes

Reaction equation

HRID 986448 reaction equation
Cl[CH2:2][CH:3]([CH3:19])[CH:4]([C:6]1[CH:18]=[CH:17][C:9]([CH2:10][C:11]2[CH:12]=[N:13][CH:14]=[CH:15][CH:16]=2)=[CH:8][CH:7]=1)[OH:5].[C:20]([O-:23])(=[O:22])[CH3:21].[Na+].[Cl-].[Na+].C(OCC)(=O)C>CN(C)C=O>[C:20]([O:23][CH2:2][CH:3]([CH3:19])[CH:4]([C:6]1[CH:18]=[CH:17][C:9]([CH2:10][C:11]2[CH:12]=[N:13][CH:14]=[CH:15][CH:16]=2)=[CH:8][CH:7]=1)[OH:5])(=[O:22])[CH3:21]

Participants

6

Reactant 4

HCID 5234Sodium ChlorideHCID 8857Ethyl AcetateHCID 517045Sodium AcetateHCID 201486153-[p-(3-Chloro-1-hydroxy-2-methylpropyl)benzyl]pyridine

Product 1

HCID 201486363-[p-(3-Acetoxy-1-hydroxy-2-methylpropyl)benzyl]pyridineYield 36.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

In 11 ml of N,N-dimethylformamide was dissolved 2.29 g of 3-[p-(3-chloro-1-hydroxy-2-methylpropyl)benzyl]pyridine, and to the resulting solution was added 1.36 g of sodium acetate, after which the resulting mixture was subjected to reaction under reflux for 2 hours. The solvent was removed by distillation under reduced pressure, and to the residue thus obtained were added 20 ml of a saturated aqueous sodium chloride solution and 20 ml of ethyl acetate. The organic layer was separated, washed with 10 ml of water, and then dried over anhydrous magnesium sulfate. The solvent was removed by distillation under reduced pressure, and the residue thus obtained was purified by a column chromatography [Wako Silica Gel C-200, eluant: chloroform] to obtain 910 mg (yield 36.7%) of colorless, oily 3-[p-(3-acetoxy-1-hydroxy-2-methylpropyl)benzyl]pyridine.

Workup

  1. customafter which the resulting mixture was subjected to reaction
  2. temperatureunder reflux for 2 hours
  3. customThe solvent was removed by distillation under reduced pressure
  4. customto the residue thus obtained
  5. customThe organic layer was separated
  6. washwashed with 10 ml of water
  7. dry with materialdried over anhydrous magnesium sulfate
  8. customThe solvent was removed by distillation under reduced pressure
  9. customthe residue thus obtained
  10. customwas purified by a column chromatography [Wako Silica Gel C-200, eluant: chloroform]

Sources & evidence

ORD record
ord-8fa4aa8a20494f3bb5df8ab7dc573b6c
Source dataset
uspto-grants-1987_12
Patent number
US04713387

Reaction notes

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