Hydrochloric Acid → HCID 54267559, compound

Participants

Reaction Conditions

Reaction Steps

A solution of the acid from Step 1 (17.88 g, 58.7 mmol) and triethylamine (9.53 g, 94.2 mmol) was dissolved in 50 mL of anhydrous toluene, cooled to 0° C. and treated with diphenylphosphoryl azide (16.46 g, 59.8 mmol). The solution was maintained at 0° C. for 36 minutes and warmed to room temperature for 4 hours. The reaction was poured into water, extracted with ether, dried over magnesium sulfate, and concentrated in vacuo to remove the ether. The remaining toluene solution was heated to 110° C. for 1 hour. Tert-Butyl alcohol (7 mL, 74 mmol) was added to the reaction mixture. After an additional twenty minutes, concentrated hydrochloric acid (5 mL) was cautiously added and the reaction maintained at 90° C. for 16 hours. The solution was concentrated in vacuo and the residue taken up in ethyl acetate, washed with water, sat. aq. NaHCO3, and brine, dried over anhydrous MgSO4, filtered and concentrated in vacuo to provide the ketone as an orange oil (14.62 g, 90%) that was used in the next step without further purification: 1H NMR (CDCl3) 300 MHz 7.40-7.10 (m,8H), 4.20 (s, 2H), 2.46 (s, 3H).

Provenance & Evidence