2-(2-Hydroxyethyl)pyridine → 2-(2-((6-Bromohexyl)oxy)ethyl)pyridine

HRID 1032706Notes

Reaction equation

HRID 1032706 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[CH2:7][CH2:8][OH:9].[Br:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16]Br.[OH-].[Na+]>S([O-])(O)(=O)=O.C([N+](CCCC)(CCCC)CCCC)CCC.O>[Br:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][O:9][CH2:8][CH2:7][C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][N:1]=1

Participants

6

Reactant 3

HCID 76752-(2-Hydroxyethyl)pyridineHCID 123681,6-DibromohexaneHCID 14798Sodium Hydroxide

Product 1

HCID 151669352-(2-((6-Bromohexyl)oxy)ethyl)pyridine

Reagents, catalysts & solvents 2

HCID 94433Tetrabutylammonium hydrogen sulfateCatalystHCID 962WaterSolvent

Procedure

A mixture of 2-pyridineethanol (5 g), 1,6-dibromohexane (20 ml), 50% (w/v) sodium hydroxide (20 ml) and tetra-n-butylammonium hydrogen sulphate (500 mg) was stirred at room temperature for 6 h, Water (100 ml) was added and the mixture was extracted with ether (2×100 ml). The organic extracts were washed with water and brine, dried and concentrated to an oil which was purified by FCC eluting with hexane→hexane-ether(1:1) to give the title compound as a colourless oil (6.6 g), t.l.c. (hexane-ether 1:1) Rf 0.19.

Workup

  1. extractionthe mixture was extracted with ether (2×100 ml)
  2. washThe organic extracts were washed with water and brine
  3. customdried
  4. concentrationconcentrated to an oil which
  5. customwas purified by FCC
  6. washeluting with hexane→hexane-ether(1:1)

Sources & evidence

ORD record
ord-c825e2d1a9534e9393448f9f8a532402
Source dataset
uspto-grants-1990_09
Patent number
US04959381

Reaction notes

Loading…