Reacción #549478

Ecuación de reacción

ethanol

4-carboxy-4-(2-thienyl)cyclohexanone ethylene ketal

triethylamine

diphenylphosphonic azide

→

4-(2-thienyl)-4-ethoxycarbonylaminocyclohexanone ethylene ketal

Rendimiento 51.0%

Condiciones de reacción

Tratamiento posterior

1. 1
   Temperatura' heating
2. 2
   Temperaturaat reflux the bulk of the solvent
3. 3
   Otrois removed in vacuum
4. 4
   workup.DISSOLUTIONThe residue is dissolved in water
5. 5
   LavadoThe organic layer is washed in turn with water, ice cold 2.5 N hydrochloric acid, water, saturated sodium bicarbonate and brine ad
6. 6
   OtroThe residual solid is recrystallized from cyclohexane
7. 7
   Otroto give 1.58 g

Procedimiento

To a solution of 2.68 g. (0.010 mole) of 4-carboxy-4-(2-thienyl)cyclohexanone ethylene ketal and 1.39 ml. triethylamine in 40 ml. ethanol there is added 2.75 g. diphenylphosphonic azide. Following 5 hours' heating at reflux the bulk of the solvent is removed in vacuum. The residue is dissolved in water and ether:benzene. The organic layer is washed in turn with water, ice cold 2.5 N hydrochloric acid, water, saturated sodium bicarbonate and brine ad taken to dryness. The residual solid is recrystallized from cyclohexane to give 1.58 g. (51% yield) of 4-(2-thienyl)-4-ethoxycarbonylaminocyclohexanone ethylene ketal, m.p. 113°-117° C.

Fuente