Chloroform → HCID 59526358, compound

Participants

Reaction Conditions

Reaction Steps

A solution of t-BuOK (9.07 g, 81 mmol) in THF (50 mL) was cooled to −78° C. before adding DMF (70 mL). A solution of 3-(5-nitro-2-thienyl)-1-{[2-(trimethylsilyl)ethoxy]methyl}-1H-1,2,4-triazole (6.60 g, 20.22 mmol) and CHCl3 (1.79 mL, 22.24 mmol) in DMF (35 mL) was added dropwise over 1 h. After complete addition, the reaction was stirred at −78° C. for 30 min, quenched with 2 N HCl, allowed to warm to room temperature, and extracted with EtOAc (2×). The combined organic layers were washed with brine, dried (MgSO4), filtered, and evaporated. Purification of the crude residue by flash chromatography (0-25% EtOAc/hexanes) afforded the title compound as a yellow solid.

Provenance & Evidence