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ChemicalBook CAS DataBase List DIETHYL 2-(PHENYLETHYL)MALONOATE

DIETHYL 2-(PHENYLETHYL)MALONOATE synthesis

12synthesis methods
-

Yield:-

Reaction Conditions:

with potassium tert-butylate in N-methyl-acetamide;water

Steps:

1.A Tert-butyl 3-{1-[2'-(ethoxycarbonyl)-4'-phenylbutyl]cyclopentane-1'-carbonylamino}-2,3,4,5-tetrahydro-2-oxo-1H-1-benzazepine-1-acetate.
A) 123.4 g of potassium tert-butoxide were added in portions to a solution of 160.1 g of diethyl malonate in one liter of dimethylformamide at a temperature of 15° C. The reaction mixture was stirred for 30 min and then, at room temperature, a solution of 207.7 g of phenethyl bromide in 200 ml of dimethylformamide was added dropwise. The reaction mixture was subsequently heated at 60° C for one hour and left to cool again. The dimethylformamide was evaporated under reduced pressure, and the residue was taken up in a mixture of methyl tert-butyl ether and water. The organic phase was separated, washed with water, dried over sodium sulfate and evaporated. The crude product remaining as an oily residue was purified by distillation under reduced pressure. 202.5 g of ethyl 2-ethoxycarbonyl-4-phenylbutanoate were obtained, boiling point at 1.5 Torr=148°-153° C.

References:

Solvay Pharmaceuticals GmbH US5677297, 1997, A

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