Hydrochloric Acid → HCID 11137342, compound

Participants

Reaction Steps

A solution of n-butyllithium (10.0 ml, 10.0M in hexane, 0.10 mol) is added dropwise to a stirred cooled (-5° to 0° C.) solution of pent-1-yne (6.80 g, 0.10 mol) in dry THF under dry nitrogen. This mixture is stirred for 10 minutes and then a solution of dry zinc chloride (13.63 g, 0.10 mol) in dry THF is added dropwise to 2-bromothiophene (16.00 g, 0.098 mol) at a temperature of between -5° C. and 0° C. followed by addition of tetrakis (triphenylphosphine)palladium(O) (3.40 g, 2.94 mol). The mixture is stirred at room temperature overnight (glc analysis revealing a complete reaction) and poured into 10% hydrochloric acid. The product is extracted into ether (×2) and the combined ethereal extracts are washed with aqueous sodium hydrogen carbonate and dried (MgSO4). The solvent is removed in vacuo, then the product is filtered and distilled to yield 12.9 g (88%) colourless liquid.

Provenance & Evidence