tert-Butanol → HCID 18667078, compound

Participants

Reaction Steps

To a solution of N-trifluoroacetyl-N-2-heptylamine(6.33 g, 30 mmol) in CH3CN (75 ml)/t-butanol(0.5 ml) was added 18-crown-6(300 mg) and powdered potassium t-butoxide (3.36 g, 30 mmol). After stirring for 15 min most of the solids had dissolved and propargyl bromide (80% in toluene) (3.5 ml, 31.5 mmol) was then added dropwise. The solution was stirred at 80-85° C. (oil bath temperature) for 24 h during which time the solution became brown in color and a white solid precipitated. After the reaction mixture had cooled to room temperature, dichloromethane (75 ml) was added and the solids were filtered with suction and washed with dichloromethane. The weight of the solids (KBr) was 3.6 g (theoretical: 3.57 g). The combined filtrates were rotary evaporated to give 7.3 g of a dark brown liquid (theoretical yield=7.47 g). The product was not purified but used directly in the next step.

Provenance & Evidence