Pyrrolidine → 2-[4-(Pyrrolidin-1-yl)phenyl]ethan-1-ol

Participants

Reaction Conditions

Reaction Steps

A solution of 2-(4-bromophenethoxy)tetrahydro-2H-pyran (28.01 g, 98.39 mmol) in toluene (100 ml) and pyrrolidine (9.93 ml, 119 mmol) were added to a mixture of dry palladium acetate (270 mg, 1.20 mmol), 2-(di-t-butylphosphino)biphenyl (720 mg, 2.40 mmol) and sodium t-butoxide (14.42 g, 150 mmol), and they were stirred at 70° C. for 12 hours. Water was added to the reaction mixture. After the extraction with ethyl acetate, the product was extracted from the organic layer with 1 M hydrochloric acid. The aqueous layer was neutralized with an aqueous sodium hydroxide solution and extracted with ethyl acetate. The organic layer was dried to obtain 4-pyrrolidinophenethyl alcohol in the form of a light yellow solid (16.41 g, 87%).

Provenance & Evidence