Hydrochloric Acid → 1-Undecyn-3-ol, 1-(trimethylsilyl)-

Participants

Reaction Conditions

Reaction Steps

173 mol of n-butyllithium solution (1.6 mol in hexane) is instilled in a solution of 25 g of trimethylsilylacetylene in 500 ml of tetrahydrofuran with stirring and argon atmosphere at -40° C., is stirred for 30 minutes at -40° C., cooled to -70° C. and 48.1 ml of nonanal is instilled at this temperature. After an hour at -70° C., the mixture is allowed to come to -30° C., 300 ml of 2 n hydrochloric acid is added and shaken with diethyl ether. The organic phases are dried (Na2SO4), concentrated by evaporation and the residue is distilled in a bulb tube at 120°-130° C./0.2 mbar. Thus 48.5 of (3RS)-1-(trimethylsilyl)-1-undecin-3-ol is obtained as a colorless oil.

Provenance & Evidence