Potassium tert-butoxide → HCID 57687394, compound

Participants

Reaction Conditions

Reaction Steps

Potassium tert-butoxide (2.36 g, 21 mmol) was slowly added to a stirred solution of example 1b (6.62 g, 20 mmol) in 1:1 THF/dioxane (60 mL) at 0° C. The reaction mixture was stirred at 0° C. for 5 h. The precipitate was collected by filtration to give 5.22 g (79%) of clean desired product as a beige solid. The filtrate contained product contaminated with some starting material and was concentrated in vacuo. The residue (1.3 g) was treated by potassium tert-butoxide (350 mg, 3.12 mmol) in 1:1 THF/dioxane (60 mL) for 18 h. Purification by silica gel chromatography gave an additional 1.1 g (18%) of the title compound as a beige solid. 1H NMR (400 MHz, DMSO-d6): δ 8.41 (s, 1H), 8.09-8.19 (m, 1H), 4.21 (q, 211, J=7.2 Hz), 3.88-3.97 (m, 1H), 1.27 (t, 3H, J=7.2 Hz), 1.08-1.14 (m, 4H). MS (ES) [m+H] calc'd for C15H12F3NO3, 312; found 312.

Provenance & Evidence