Dimethylformamide → HCID 53884252, compound

HRID 2408871Notes

Reaction equation

HRID 2408871 reaction equation
CN(C=O)C.[N:6]1[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=1[OH:12].Br[CH2:14][CH2:15][CH2:16][CH2:17][Cl:18].C(=O)([O-])[O-].[K+].[K+]>C(OCC)(=O)C.O>[Cl:18][CH2:17][CH2:16][CH2:15][CH2:14][O:12][C:7]1[CH:8]=[CH:9][CH:10]=[CH:11][N:6]=1

Participants

7

Reactant 4

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 813641-Bromo-4-chlorobutaneHCID 178516071HCID 178516071, compound

Product 1

HCID 53884252HCID 53884252, compoundYield 17%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a DMF solution (110 ml) containing 2-pyridinol (10 g, 105 mmol) and 1-bromo-4-chlorobutane (36 ml, 315 mmol) was added potassium carbonate (16 g, 116 mmol), followed by stirring at room temperature for 8 hours. Water (300 ml) was added to the reaction solution, and extraction with ethyl acetate (300 ml) was then conducted. The organic layer was washed with water (300 ml) twice and dried over magnesium sulfate. The solvent was distilled off, under reduced pressure, and the residue was then purified by silica gel column chromatography (n-hexane:ethyl acetate=5:1). The purified product was concentrated under reduced pressure to thereby obtain 3.32 g of oily colorless 2-(4-chlorobutoxy)pyridine.

Workup

  1. washThe organic layer was washed with water (300 ml) twice
  2. dry with materialdried over magnesium sulfate
  3. distillationThe solvent was distilled off, under reduced pressure
  4. customthe residue was then purified by silica gel column chromatography (n-hexane:ethyl acetate=5:1)
  5. concentrationThe purified product was concentrated under reduced pressure

Sources & evidence

ORD record
ord-5a8d81ef9f91471e99dbefbd78b70082
Source dataset
uspto-grants-2014_08
Patent number
US08815871B2

Reaction notes

Loading…