Water → HCID 53859849, compound

Participants

Reaction Steps

The product of Example 38 (0.3 g, 0.79 mmol) was dissolved in THF (10 mL) to which carbonyldiimidazole (0.129 g, 0.79 mmol) was added. The solution was stirred at room temperature for one hour, at which time 2,2,2-trifluoroethanol (10 mL) was added and the solution stirred overnight at room temperature. The solution was poured into 4-5 volumes of water and extracted with Et2O (2×100 mL). The organics were dried over MgSO4 and concentrated to a yellow-brown oil (0.19 g). Crude product was chromatographed using silica gel (230-400 mesh) with descending solvent gradient from 100% petroleum ether to 80/20 petroleum ether/ethyl acetate as the mobile phase. Elution and concentration gave α-(methoxyimino)-N-methyl-2-[[[3-chloro-5-(2,2,2-trifluoroethoxycarbonyl)-2-pyridinyl]oxy]methyl]-benzeneacetamide (0.09 g) as a green oil.

Provenance & Evidence