N,N,N',N'-Tetramethylethylenediamine → 7-Oxo-5,6,7,8-tetrahydronaphthalene-2-carbonitrile

Participants

Reaction Conditions

Reaction Steps

A solution of 7-bromo-3,4-dihydronaphthalen-2(1H)-one (500 mg, 2.2 mmol) in 5 mL of anhydrous DMF in a 10 mL CEM microwave tube was added Zn(CN)2 (515 mg, 4.4 mmol), Pd2(dba)3 (55 mg, 0.034 mmol), TMEDA (55 mg, 0.47 mmol) and Xantphos (29 mg, 0.05 mmol) sucessively. The reaction tube was sealed and heated to 160° C. under microwave irradiation with a 5 min hold time and 300 W maxium power input. After cooling under a stream of compressed air, the reaction mixture was washed with EtOAc through a Celite® with a thin layer of silica gel in the middle size. The filtrate was washed with saturated bine, dried over anhydrous sodium sulfate and concentrated. The residue was purified by preparative TLC to afford 7-oxo-5,6,7,8-tetrahydronaphthalene-2-carbonitrile (150 mg, yield 40%).

Provenance & Evidence