Ethylene carbonate → 2-{2-[2-(Dimethylamino)ethoxy]phenoxy}ethanol

Participants

Reaction Conditions

Reaction Steps

To dry DMF (50 mL) was added 2-[2-(dimethylamino)ethoxy]phenol (from Step 1; 5.4 g, 28.0 mmol), ethylene carbonate (3.20 g, 36.4 mmol) and potassium carbonate (3.9 g, 28 mmol) and the mixture was heated at 155° C. for one hour 30 minutes. The solvent from the filtered solution was evaporated under reduced pressure and the resulting residue was dissolved in CHCl3 (50 mL) and filtered through a plug of silica (50 mm×50 mm) using CHCl3 (50 mL) followed by CHCl3/MeOH (95:5) as eluents. Solvents from the pure fractions were removed under reduced pressure to give 4.8 g (76%) of the title compound as a light brown oil. HRMS m/z calcd for C12H19NO3 (M)+ 225.1365. found 225.1363.

Provenance & Evidence