Hydrochloric Acid → HCID 53875126, compound

Participants

Reaction Conditions

Reaction Steps

(+/-)-1,5-dimethyl-3-(p-hydroxyphenyl)-3-phenyl-2-pyrrolidone (from Example 1), 1.5 g, was dissolved in 30 mL dichloromethane. The flask was flushed with argon and chilled in an acetone/dry ice bath to -60° C. I M boron tribromide in dichloromethane, 10 mL, was then added drop-wise over 18 min with stirring. The reaction was allowed to come to room temperature and stirred for 22 h. Methanol, 10 mL, was then added slowly to quench the reaction. The resultant solution was rotary evaporated to give an oil redissolved in 10 mL methanol and rotary evaporated a second time. The oil was diluted with 20 mL water to give a precipitate. 6 N hydrochloric acid, 6 mL, was added followed by 50 mL dichloromethane. Mixing gave a biphasic solution. The phases were separated and the upper aqueous phase was reextracted twice with 25 mL portions of dichloromethane. The combined dichloromethane extracts were washed with saturated sodium chloride solution, dried over sodium sulfate, and evaporated to give a foam residue.

Provenance & Evidence