Ethyl phenylacetate → Dimethyl 1-(4-methoxyphenyl)-1,2-cyclopropanedicarboxylate

Participants

Reaction Conditions

Reaction Steps

To a stirred slurry of of NaH (4.4 g, 60% in mineral oil) in anhydrous Et2O (0.3 l) was added methanol (10.3 mL) followed by a solution of bromo ester obtained in Prep. 1 methyl bromo(4-methoxyphenyl)acetate (29 g) in methyl acrylate (19.8 mL) (for examples starting from an ethyl phenylacetate derivative ethanol and ethyl acrylate were used, respectively) and methanol (3 mL) at 0° C., over a 30 min. The mixture was stirred at 25° C. for 24 h and then unreacted NaH was decomposed with 3 mL methanol. Water was added (75 mL), the organic phase separated, dried over Na2SO4 and filtered. Volatiles were evaporated in vacuo to give 31.5 g of the title compound as an oil, which was used in the subsequent step without further purification.

Provenance & Evidence