Propargyl alcohol → HCID 19843629, compound

Participants

Reaction Steps

To a solution of 2-propynol (0.65 g/0.68 ml, 11.7 mmol) in 25 ml of tetrahydrofuran (THF), cooled to -60°, is slowly added butyllithium in hexane (14.6 ml, 23.3 mmol) over 5 min. About 5 ml of HMPA is added and the mixture is warmed to -20° and stirred for 5 min. The mixture is then cooled again to -60° and octylthiocyanate (2.0 g, 11.7 mmol) in 3 ml of THF is added over 1 min. The mixture is allowed to warm to RT over 1 hour and is stirred at RT for an additional hour. It is then cooled to -10° and quenched with water. The reaction mixture is diluted with ether, washed with water and brine and dried to give 3-octylthio-2-propynol.

Provenance & Evidence