Triacetoxyperiodinane → HCID 22170988, compound

Participants

Reaction Steps

To a solution of Dess-Martin periodinane (2.0 g, 4.6 mmol, 2.0 equiv) in CH2Cl2 (10 mL) was added a solution of [5-(3,4-dichloro-phenyl)-1-(4-ethoxy-phenyl)-1H-pyrazol-3-yl]-methanol (prepared by the method of Example 1, Steps A-C; 0.84 g, 2.3 mmol) in CH2Cl2 (10 mL). The reaction mixture was stirred overnight at room temperature. Then the reaction was quenched with 1 M NaOH (10 mL), and the resulting mixture was stirred until the layers separated. The aqueous layer was back-extracted with CH2Cl2 (3×10 mL). The combined organic layers were washed with 1 M NaOH (20 mL) then H2O (20 mL), dried (MgSO4), and concentrated to provide the pure aldehyde as a dark brown oil (0.59 g, 1.6 mmol, 70%). TLC (silica gel, 1:1 EtOAc/hexanes): Rf=0.62. MS (ESI): mass calculated for C18H14Cl2N2O2, 360.04; m/z found, 361 [M+H]+. 1H NMR (400 mHz, CDCl3): 10.05 (s, 1H), 7.38-7.36 (m, 2H), 7.25-7.21 (m, 2H), 7.0 (s, 1H), 7.0-6.97 (m, 1H), 6.93-6.91 (m, 2H), 4.06 (q, J=7.0 Hz), 1.44 (t, J=7.0 Hz, 3H).

Provenance & Evidence