Pyridine → 4-Triphenylmethoxy-1-Octyne

Participants

Reaction Steps

A mixture of 10 g. (0.08 moles) of 4-hydroxy-1-octyne [L. Crombie and A. G. Jacklin, J. Chem. Soc., 1632 (1937), also Example 87] and 30.75 g. (0.09 moles) of triphenylmethyl bromide in 85 ml. of dry pyridine is heated on the steam bath for 2 hours. The cooled mixture is treated with water and extracted with ether. The extract is washed successively with ice cold 2% hydrochloric acid, saturated sodium chloride solution, dried with magnesium sulfate, and taken to dryness. Column chromatography of the residue on Florisil affords an oil; λmax 3.01, 4.72 (acetylenic hydrogen), 6.28, 9.65 and 14.25 μ (triphenylmethoxy group).

Provenance & Evidence