Tetrahydrofuran → HCID 19881174, compound

Participants

Reaction Steps

To 250 mL of THF was added 14 g (67 mmol) of 6-bromoquinoline and 44 mL (88 mmol) of 2M butyllithium in pentane was added at -70° under argon. The reaction was stirred for 15 minutes and 28.4 g (87.2 mmol) of tributyltin chloride was added at such a rate that the temperature remained below -60° . When addition was complete, the mixture was allowed to warm to -50° at which point the dark orange color characteristic of the anion became light amber. The mixture was stirred for 14 hrs at -70° and poured into ice-water and ether. The layers were separated, the ether layer washed with water, dried with magnesium sulfate, filtered and concentrated. The resultant oil was chromatographed on a silica gel column (30 cm ×6 cm) using 30% ether in hexane to provide 17.8 g (63%) of 6-quinolinyltributylstannane.

Provenance & Evidence