Triacetoxyperiodinane → 5'-Isopropyl-2'-methoxy-4-(trifluoromethyl)biphenyl-2-carbaldehyde

Participants

Reaction Steps

To a solution of 0.725 g of [5′-isopropyl-2′-methoxy-4-(trifluoromethyl)biphenyl-2-yl]methanol in 10 mL of CH2Cl2 was added 1.14 g of Dess-Martin periodinane. The mixture was stirred at room temperature for 30 min, then filtered and concentrated. The residue was purified by flash chromatography on a Biotage Horizon, 40S column, eluting with 1 CV of 1% EtOAc in hexanes, followed by a linear gradient of EtOAc in hexanes from 1 to 100% over 10 CV to provide the title compound. Mass spectrum (ESI) 323.2 (M+1). 1H NMR (500 MHz, CDCl3): δ 9.81 (s, 1H), 8.28 (s, 1H), 7.88 (dd, J=1.5 Hz, 8 Hz, 1H), 7.54 (d, J=8 Hz, 1H), 7.33 (dd, J=2 Hz, 8 Hz, 1H), 7.16 (d, J=2.5 Hz, 1H), 6.95 (d, J=8.5 Hz, 1H), 3.74 (s, 3H), 2.95 (septet, J=7 Hz, 1H), 1.29 (d, J=7 Hz, 6H).

Provenance & Evidence