1,6-Dibromohexane → 2-[3-[(6-Bromohexyl)oxy]propyl]pyridine

HRID 1088708Notes

Reaction equation

HRID 1088708 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[CH2:7][CH2:8][CH2:9][OH:10].[Br:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17]Br.[OH-].[Na+]>O>[Br:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][O:10][CH2:9][CH2:8][CH2:7][C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][N:1]=1

Participants

5

Reactant 3

HCID 123681,6-DibromohexaneHCID 14798Sodium HydroxideHCID 72922Pyripropanol

Product 1

HCID 221617422-[3-[(6-Bromohexyl)oxy]propyl]pyridine

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 2-pyridinepropanol (15.8 g), 1,6-dibromohexane (60 ml), 50% (w/v) sodium hydroxide (60 ml) and TAB (1.5 g) was stirred at room temperature for 5 h. Water (200 ml) was added and the mixture was extracted with ether (2×200 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 (18.1 g), t.l.c. (hexane-ether 1:1) Rf 0.19.

Workup

  1. extractionthe mixture was extracted with ether (2×200 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-f5a002352d35445fb9e05ce79e852b4f
Source dataset
uspto-grants-1990_10
Patent number
US04963564

Reaction notes

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