Reacción #5673

Ecuación de reacción

oxazolidinone

(R*,S*)-(±)-5-(3-chlorophenyl)-3-(2 -(3, 4-dihydroxyphenyl)-1-methylethyl)-2-oxazolidinone

diethyl dibromomalonate

potassium carbonate

→

(R*,S*)-(±)-5-(2-(5-(3-chlorophenyl)-2-oxo-3-oxazolidinyl)propyl)-1,3-benzodioxole-2,2-dicarboxylic acid, diethyl ester

Rendimiento 66.1%

Disolventes

acetone

Condiciones de reacción

Tratamiento posterior

1. 1
   FiltraciónThe mixture is filtered
2. 2
   Lavadowashed with acetone
3. 3
   Lavadothe combined filtrate and wash
4. 4
   Otroare evaporated to a yellow oil
5. 5
   OtroThe oil is purified by flash chromatography
6. 6
   Lavadoeluting with 5 percent acetone in toluene
7. 7
   Otroevaporated

Procedimiento

A mixture of 0.8 g of the above oxazolidinone, 0.74 g of diethyl dibromomalonate, 1.2 g of anhydrous potassium carbonate and 20 ml of acetone are stirred overnight with the addition of a few drops of diethyl dibromomalonate. The mixture is filtered, washed with acetone and the combined filtrate and wash are evaporated to a yellow oil. The oil is purified by flash chromatography, eluting with 5 percent acetone in toluene. The pure fractions are combined and evaporated, giving 766 mg of (R*,S*)-(±)-5-(2-(5-(3-chlorophenyl)-2-oxo-3-oxazolidinyl)propyl)-1,3-benzodioxole-2,2-dicarboxylic acid, diethyl ester as a colorless oil.

Fuente