Ethyl bromoacetate → HCID 17761463, compound

Participants

Reaction Steps

3,4-Dihydro-6,7-dimethoxy-1(2H)-naphthalenone (10.0 g) was dissolved in tetrahydrofuran (200 ml), and thereto was added dropwise a 2M solution of lithium diisopropylamide in tetrahydrofuran (37 ml) at -70° C. The mixture was stirred for 30 minutes, and thereto was added dropwise ethyl bromoacetate (10.5 g) at -70° C. The mixture was stirred at the same temperature for two hours, and then stirred at 20° C. overnight. The reaction mixture was poured into ice-water, and extracted with diethyl ether. The ether layer was washed successively with water, 10% hydrochloric acid and 10% aqueous sodium hydrogen carbonate solution, and dried over anhydrous sodium sulfate. The resultant was concentrated under reduced pressure to remove the solvent to give ethyl 1,2,3,4-tetrahydro-6,7-dimethoxy-1-oxo-2-naphthaleneacetate (12.0 g) as an oily product.

Provenance & Evidence