Sodium periodate → HCID 69944598, compound

Participants

Reaction Steps

5-[(1S,2S)-1-Acetoxy-2-(3,4-dichlorophenyl)-4-oxobutyl]-1-phenylpyrazole.A solution of 5-[(1S,2S)-1-acetoxy-2-(3,4-dichlorophenyl)-4-pentenyl]-1-phenylpyrazole (90 mg) in tetrahydrofuran (1 mL), diethyl ether (2 mL) and water (2 mL) was treated with osmium tetraoxide (0.07 mL of a 0.2M solution in water) and sodium periodate (100 mg). The resulting biphasic mixture was stirred vigorously at room temperature for 4 hours. The mixture was diluted with water and extracted with ethyl acetate. The organic extracts were washed (brine), dried, and evaporated to afford the title compound as a pale amber foam (89 mg). This material was used immediately; NMR: 9.57 (s,1), 7.62 (d,1), 7.45-7.21 (m,6), 6.99 (d,1), 6.72 (dd,1), 6.31 (d,1), 6.15 (d,1), 3.63 (m,1), 2.77 (m,2), 2.03 (s,3); MS: m/z=419((M+1), 37Cl), 417((M+1), 35Cl).

Provenance & Evidence