Methanol → HCID 68539933, compound

Participants

Reaction Steps

To a solution of 4-{[2-{4-[(phenylmethyl)oxy]phenyl}-3-(trifluoromethyl)-1-naphthalenyl]oxy}benzaldehyde (187) (0.23 g, 0.45 mmol) in MeOH (4 mL) and CH2Cl2 (2 mL) was added NaCN (0.12 g, 2.26 mmol) followed by MnO2 (0.56 g, 5.42 mmol). The reaction mixture was stirred at room temperature overnight, diluted with EtOAc (50 mL) and filtered through a pad of celite on top of a layer of silica gel. The filtrate was washed with water, brine, dried over Na2SO4, filtered, and concentrated to give the crude product as a light yellow solid, which upon trituration with 1% MeOH in hexanes, gave 0.21 g (86%) of the title compound (188) as a white solid. mp 131-132° C. 1H NMR (400 MHz, CDCl3): δ 3.85 (s, 3H), 5.01 (s, 2H), 6.58 (d, J=8.8 Hz, 2H), 6.83 (d, J=8.6 Hz, 2H), 7.05 (d, J=8.6 Hz, 2H), 7.30-7.44 (m, 5H), 7.55-7.66 (m, 2H), 7.79 (d, J=8.8 Hz, 2H), 7.89 (d, J=8.2 Hz, 1H), 8.03 (d, J=8.1 Hz, 1H), 8.24 (s, 1H). LCMS (ESI): m/z 551 (M+Na)+.

Provenance & Evidence