Oxolane--water (1/1) → HCID 86623619, compound

Participants

Reaction Steps

A solution of 49 mg (0.12 mmol) of 1-(4-(5-(4-isopropoxy-3-(trifluoromethyl)phenyl)-1,2,4-oxadiazol-3-yl)-3-methylphenyl)ethane-1,2-diol and 37 mg (0.17 mmol) of sodium periodate in 9 mL of 2:1 v:v THF/H2O mix solvent. After stirring at rt for 4 h, the mixture was poured into brine and extracted with EtOAc (3×10 mL). Organic layers were combined, dried over MgSO4, and concentrated. Chromatography on Biotage 40S cartridge using 1:9 v/v EtOAc/hexanes as the eluant afforded 40 mg of the title compound: 1H NMR (500 MHz, CDCl3) δ 1.44 (d, J=5.9, 6H), 2.78 (s, 3H), 4.79 (m, 1H), 7.16 (d, J=9.0, 1H), 7.84-7.86 (m, 2H), 8.28 (d, J=8.5, 1H), 8.32 (dd, J=2.2, 8.9, 1H), 8.44 (d, J=2.1, 1H), 10.09 (s, 1H).

Provenance & Evidence