Sodium Hydroxide → Ammonia

Participants

Reaction Conditions

Reaction Steps

A solution of 4-(methylthio)phenylacetonitrile (828 mg, 5.08 mmol) in tetrahydrofuran (10 mL) was added dropwise to lithium aluminium hydride (1M in tetrahydrofuran, 5.6 mL, 5.6 mmol) and the mixture was stirred for 1 hour at 0° C. Further lithium aluminium hydride (1M in tetrahydrofuran, 5.6 mL, 5.6 mmol) was added and the mixture was stirred at room temperature for 18 hours then heated under reflux for 1 hour. The reaction mixture was cooled to 0° C., 1M sodium hydroxide solution (3 mL) was added dropwise, and stirring continued for a further hour. The mixture was then filtered through Celite®, washing through with ethyl acetate, and the filtrate was washed with 1M sodium hydroxide solution. The organic solution was then loaded onto an Isolute® SCX cartridge, washed with methanol and eluted with 1M ammonia in methanol. The relevant fractions were concentrated in vacuo and the residue was purified by column chromatography on silica gel, eluting with dichloromethane:methanol:0.88 ammonia, 100:0:0 to 95:5:0.5, to afford the title compound as a yellow oil in 18% yield, 154 mg. 1H NMR (400 MHz, CDCl3) δ: 7.20 (2H, m), 7.14 (2H, m), 2.84 (2H, m), 2.71 (2H, m), 2.43 (3H, s) ppm; LRMS APCI m/z 168 [M+H]+

Provenance & Evidence