Water → HCID 53721501, compound

Participants

Reaction Conditions

Reaction Steps

The acid from Step 1 (9.01 g, 29.6 mmol) and triethylamine (3.03 g, 29.9 mmol) were dissolved in 45 mL of anhydrous toluene, cooled to 0° C. and treated with diphenylphosphoryl azide (8.22 g, 29.9 mmol). The solution was maintained at 0° C. for 10 minutes and warmed to room temperature for 2 hours. The reaction was poured into water, extracted with ether, dried over anhydrous MgSO4, and concentrated in vacuo to remove the ether. The remaining toluene solution was heated to 90° C. for 15 minutes. Tert-Butyl alcohol (10 mL) was added to the reaction mixture. After an additional twenty minutes, concentrated hydrochloric acid (8 mL) was cautiously added and the reaction maintained at 90° C. for 15 minutes. The solution was cooled to room temperature and a precipitate formed that was isolated by filtration, washed with ether and air dried to provide the desired ketone as a white solid (2.43 g, 30%): mp 143°-147.5° C. 1H NMR (CDCl3) 300 MHz 8.08 (d, J=8.8 Hz, 2H), 7.55 (d, J=8.5 Hz, 2H), 7.24 (m, 4H), 4.35 (s, 2H), 2.05 (s, 3H). Mass spectrum: M+H=277.

Provenance & Evidence