Diisopropylamine → 2-(2-Ethoxycarbonylethyl)-3,4-dihydro-1(2H)-naphthalenone

참여 물질

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반응 단계

To a solution of diisopropylamine (16 ml) in tetrahydrofuran (350 ml) was added dropwise a 1.6M solution of butyl lithium in hexane (71 ml) under cooling at -78° C., and the mixture was stirred for 30 minutes. To the reaction mixture was added dropwise a solution of 3,4-dihydro-1(2H)-naphthalenone (16.5 g) in tetrahydrofuran (60 ml) over a period of about 20 minutes under cooling at -78° C., and the mixture was stirred for 30 minutes. To the mixture was added dropwise a solution of ethyl 3-bromopropanoate (20.5 g) in tetrahydrofuran (60 ml) over a period of about 20 minutes, and then further stirred for 30 minutes. The reaction mixture was stirred overnight at 20° C., and diluted with diethyl ether. The mixture was washed successively with water,5% aqueous sodium hydrogen carbonate solution, and 5% hydrochloric acid, and dried over anhydrous magnesium sulfate. The resultant was concentrated under reduced pressure to remove the solvent to give ethyl 1,2,3,4-tetrahydro-1-oxo-2-naphthalene-propanoate (10.1 g) as an oily product.

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