Triacetoxyperiodinane → HCID 16202801, compound

Participants

Reaction Steps

To a solution of Dess-Martin periodinane (2.3 g, 5.5 mmol, 2.0 equiv) in CH2Cl2 (10 mL) was added a solution of [5-benzo[1,3]dioxol-5-yl-1-(2,5-dichloro-phenyl)-1H-pyrazol-3-yl]-methanol (prepared by the method of Example 1, Steps A-C; 1.0 g, 2.8 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 (1.04 g, 2.8 mmol, 99%). HPLC: Rt=5.35 (Method B). MS (ESI): mass calculated for C17H10Cl2N2O3, 360.01; m/z found, 361 [M+H]+. 1H NMR (400 mHz, CDCl3): 10.05 (s, 1H), 7.50-7.43 (m, 1H), 7.25-7.21 (m, 2H), 7.7-7.26 (m, 1H), 6.96 (s, 1H), 6.74-6.72 (m, 1H), 6.68-6.65 (m, 2H), 5.97 (s, 2H).

Provenance & Evidence