octyl thiocyanate

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 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. over 5 min the mixture is warmed to -20° The mixture is then cooled again to -60° is stirred at RT for an additional hour It is then cooled to -10° quenched with water The reaction mixture is diluted with ether washed with water and brine dried

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 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. over 5 min the mixture is warmed to -20° The mixture is then cooled again to -60° is stirred at RT for an additional hour It is then cooled to -10° quenched with water The reaction mixture is diluted with ether washed with water and brine dried

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a mixture of potassium thiocyanate (5.07 g, 51.7 mmol) in 30 ml of dimethylformamide (DMF) is added 1-bromooctane (5.0 g, 4.5 ml, 25.8 mmol). The mixture is stirred at 45° for 1.5 hours. It is then cooled to 0° and water and ether are added. The ether layer is washed with water and brine and stripped to give octylthiocyanate. It is then cooled to 0° The ether layer is washed with water and brine

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a mixture of potassium thiocyanate (5.07 g, 51.7 mmol) in 30 ml of dimethylformamide (DMF) is added 1-bromooctane (5.0 g, 4.5 ml, 25.8 mmol). The mixture is stirred at 45° for 1.5 hours. It is then cooled to 0° and water and ether are added. The ether layer is washed with water and brine and stripped to give octylthiocyanate. It is then cooled to 0° The ether layer is washed with water and brine