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

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

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.