Butylamine → HCID 86746682, compound

Participants

Reaction Steps

To a 1 L flask under Argon was added CuI (5.24 g, 27 mmol) and Pd(PPh3)4 (4.9 g, 4 mmol) and the catalyst covered with 500 mL of degassed THF. To this solution was added the product of step (a) (42.7 g, 220 mmol) and degassed butylamine (44 mL, 440 mmol). To this solution was added trimethylsilyl acetylene (29 g, 290 mmol) and the reaction mixture was stirred for 7 h. Air was bubbled through the solution for 15 min and the reaction mixture filtered through celite and washed with pentane. The filtrate was washed several times with water and the aqueous fractions extracted with ether. The organic fractions were combined, dried (MgSO4) and concentrated. The residue was chromatographed over silica gel (hexane) to give 35.1 g of a tan oil (62%).

Provenance & Evidence