Diethyl 2-(6-methoxy-1-oxo-1,2,3,4-tetrahydro-naphthalen-2-yl)-2-methylmalonate synthesis
- Product Name:Diethyl 2-(6-methoxy-1-oxo-1,2,3,4-tetrahydro-naphthalen-2-yl)-2-methylmalonate
- CAS Number:1225228-88-5
- Molecular formula:C19H24O6
- Molecular Weight:348.39
Yield:-
Reaction Conditions:
Stage #1: Diethyl methylmalonatewith sodium hydride in N,N-dimethyl-formamide at 0 - 5;Inert atmosphere;
Stage #2: 2-bromo-6-methoxy-1-tetralone in N,N-dimethyl-formamide at -3;Inert atmosphere;
Stage #3: with hydrogenchloride in water;N,N-dimethyl-formamide; pH=4 - 5;Inert atmosphere;
Steps:
2
To 6 L of ice cold DMF was added 183 grams of NaH; the mixture stirred and a solution of 81 1.2 grams diethyl methylmalonate in 1.5 L DMF was added dropwise. The temp was kept at 0-5 0C for 2hrs, and then cooled below -3 0C, and 650 grams bromo-6- methoxy-3,4-dihydronaphthalen-l(2H)-one was added. The reaction was followed by HPLC until the starting material disappeared. The mixture was poured onto ice water, adjusted to pH 4-5 with HCl, and extracted with ethyl acetate. The organic layer was washed with brine, dried, decolorized and concentrated. To the residue was added ether, the mixture cooled, filtered, and the residue washed with petroleum ether to get 745 g of diethyl 2-methyl-2-(6-methoxy-l-oxo-l ,2,3,4-tetrahydronaphthalen-2-yl)malonate, M=348.2, purity 96.57%.
References:
WO2010/51031,2010,A1 Location in patent:Page/Page column 22
1078-19-9
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