Triphenylphosphine → 3,4-dihydro-6-methylnaphthalen-1(2H)-one

Participants

Reaction Steps

A solution of 19 (1.4 g, 6.1 mmol), methyl boronic acid (0.6 g, 9.3 mmol), Pd(OAc)2 (0.07 g, 0.31 mmol), PPh3 (0.16 g, 0.61 mmol), and K3PO4 (5.2 g, 24 mmol) in dry THF were stirred at reflux under N2 atm overnight. After cooling at room temperature, crude was filtered through celite, concentrated by rotary evaporation, and purified by column chromatography to give 6-methyl-3,4-dihydronaphthalen-1(2H)-one (20) (88%). 1H NMR (600 MHz, CDCl3) δ 7.93 (d, J=12.0 Hz, 1H), 7.11 (d, J=12.0 Hz, 1H), 7.06 (s, 1H), 2.92 (t, J=6.0 Hz, 2H), 2.63 (t, J=12.0 Hz, 2H), 2.37 (s, 3H), 2.13-2.10 (m, 2H). GC-MS (ES) for C11H12O [M]+ 160.

Provenance & Evidence