Reacción #215508

Ecuación de reacción

hydrochloric acid

sodium hydride

methylphenylsulfone

tetrahydrofuran

methyl (1-cyclopentylethylamino)benzoate

→

4'-(1cyclopentylethylamino)-2-(phenylsulfonyl)acetophenone

Disolventes

1,2-dimethoxyethane

Condiciones de reacción

Tratamiento posterior

1. 1
   workup.ADDITIONTo this solution is added a solution of 5.0 g
2. 2
   TemperaturaThe mixture is cooled
3. 3
   workup.ADDITIONpoured onto ice
4. 4
   Extracciónextracted with chloroform
5. 5
   OtroThe organic layer is separated
6. 6
   Lavadowashed with water and saturated sodium chloride solution
7. 7
   Secadodried over anhydrous sodium sulfate
8. 8
   Concentraciónconcentrated to dryness
9. 9
   OtroThe crude solid is chromatographed on silica gel
10. 10
    Lavadoeluting with methylene chloride

Procedimiento

A solution of 864 mg. of sodium hydride and 5.3 g. of methylphenylsulfone in 20 ml. of 1,2-dimethoxyethane is stirred at 6° C. for one hour under an atmosphere of argon. To this solution is added a solution of 5.0 g. of methyl (1-cyclopentylethylamino)benzoate in 50 ml. of tetrahydrofuran and the reaction mixture is stirred at 60° C. for 1.5 hours. The mixture is cooled, poured onto ice, acidified with dilute hydrochloric acid and pH 3 and then extracted with chloroform. The organic layer is separated, washed with water and saturated sodium chloride solution, dried over anhydrous sodium sulfate and then concentrated to dryness. The crude solid is chromatographed on silica gel, eluting with methylene chloride to yield 4'-(1cyclopentylethylamino)-2-(phenylsulfonyl)acetophenone.

Fuente