Potassium Hydroxide → 4-[2-(Indan-4-yloxy)-ethyl]-5-methyl-2-phenyl-oxazole

Participants

Reaction Conditions

Reaction Steps

4.00 g of methanesulfonic acid 2-(5-methyl-2-phenyl-oxazol-4-yl)-ethyl ester [PCT Int. Appl. (2000) WO0008002] (14.22 mmol), 2.00 g of 4-indanol (14.93 mmol) and 487.6 mg of tetrabutylammonium hydrogen sulfate were dissolved in 65 ml of toluene and heated to 80° C. KOH was then slowly added (10.66 ml of a 2M solution in H2O, 21.33 mmol), keeping the temperature at 75-80° C. The resulting mixture was stirred for 4 hours at 80° C. 35 ml of water were added, the mixture stirred for another 5 minutes at 80° C. and the water phase was then removed. 20 ml of water were added to the toluene phase, the mixture stirred for 5 minutes at 80° C., and the water phase removed. The water phase was extracted 3 times with dichloromethane. The combined organic phases were dried over MgSO4 and evaporated to afford 4.90 g (100%) of 4-[2-(indan-4-yloxy)-ethyl]-5-methyl-2-phenyl-oxazole as brown solid.

Provenance & Evidence