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

Temperatur

-78 °C

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.

1. temperatureunder cooling at -78° C.
2. stirringthe mixture was stirred for 30 minutes
3. stirringfurther stirred for 30 minutes
4. stirringThe reaction mixture was stirred overnight at 20° C.
5. washThe mixture was washed successively with water,5% aqueous sodium hydrogen carbonate solution, and 5% hydrochloric acid
6. dry with materialdried over anhydrous magnesium sulfate
7. concentrationThe resultant was concentrated under reduced pressure
8. customto remove the solvent

ORD-Eintrag

ord-82bce6580d87456291f89f2ae9007809

Quelldatensatz

uspto-grants-1998_12

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US05847159