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

HRID 1088701Notes

Reaction equation

HRID 1088701 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][OH:13].[Br:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20]Br.[OH-].[Na+]>O>[Br:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][O:13][CH2:12][CH2:11][CH2:10][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 104875906-Pyridin-2-yl-hexan-1-ol

Product 1

HCID 221617582-[6-[(6-Bromohexyl)oxy]hexyl]pyridine

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

2-Pyridinehexanol (4.88 g), 1,6-dibromohexane (12.6 ml), 12.5M aqueous sodium hydroxide (25 ml) and TAB (0.45 g) were stirred rapidly at room temperature for 7 h. The mixture was diluted with water (60 ml) and extracted with diethyl ether (3×60 ml). The combined organic extracts were washed with water (60 ml) and brine (60 ml), dried and concentrated to give an oil which was purified by FCC eluting with diethyl ether-hexane (0:1→1:1) to give the title compound as a colourless oil (4.52 g), t.l.c. (ether-hexane 1:1) Rf 0.25.

Workup

  1. extractionextracted with diethyl ether (3×60 ml)
  2. washThe combined organic extracts were washed with water (60 ml) and brine (60 ml)
  3. customdried
  4. concentrationconcentrated
  5. customto give an oil which
  6. customwas purified by FCC
  7. washeluting with diethyl ether-hexane (0:1→1:1)

Sources & evidence

ORD record
ord-9824f4326c764c35bf48b60e4fc77233
Source dataset
uspto-grants-1990_10
Patent number
US04963564

Reaction notes

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