1,6-Dibromohexane → HCID 23045258, compound

Participants

Reaction Steps

A mixture of 2-[2-(2-pyridinyl)ethoxy]ethanol hydrochloride (1.55 g), 1,6-dibromohexane (5.94 g), TAB (0.5 g) and 50% sodium hydroxide (15 ml) was stirred at room temperature under nitrogen for 5 h. The mixture was diluted with water (100 ml), extracted with diethyl ether (2×150 ml) and evaporated in vacuo to give an oil. The residual oil was partitioned between 2N hydrochloric acid (100 ml) and hexane (2×100 ml). The aqueous phase was basified to pH12 with 50% sodium hydroxide, extracted with diethyl ether (2×150 ml), dried and evaporated in vacuo to give an oil. Purification by FCC eluting with System F (2:1→1:1) gave the title compound (1.62 g) as a colourless oil. T.l.c. (diethyl ether) Rf 0.40

Provenance & Evidence