Water → HCID 19027008, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 19.4 g of 4-bromo-2-ethyl-6-methylpyridine from (a) above in 275 ml of diethyl ether chilled to -70° C. under argon was added dropwise over 1/2 hour 38.8 ml of n-butyllithium while maintaining the reaction temperature below -65° C. Stirring was continued at -70° C. for 1 hour and then 22 ml (26.4 g) of tributyltin chloride in 25 ml of diethyl ether were added over 20 minutes. The mixture was allowed to warm to 20° C. and 200 ml of water was added. The ether layer was separated, dried over magnesium sulfate and concentrated in vacuo (90° C.; 50 mm). Hexane was added and the mixture was filtered and the filtrate was concentrated in vacuo (15 mm) to give the title product as a yellow liquid.

Provenance & Evidence