Reacción #2656

Ecuación de reacción

(-)-cis-4-acetoxy-cyclopent-2-enol

triethylamine

→

title compound

Rendimiento 87.3%

(-)-cis-3-acetoxy-cyclopentanol

Rendimiento 87.3%

Disolventes

ethanol

Condiciones de reacción

Tratamiento posterior

1. 1
   Lavadopreviously washed with water (2×50 mL) and ethanol (2×50 mL), Ra
2. 2
   workup.ADDITIONCharge the atmosphere with hydrogen at 50 psi (344.74 kPa) and shake the mixture
3. 3
   Filtraciónfilter the solution
4. 4
   ConcentraciónAfter one hour concentrate the solution under vacuum
5. 5
   workup.DISTILLATIONdistill the residue
6. 6
   workup.DISTILLATIONby Kugelrohr distillation (60°-80° C., 1 mm Hg)

Procedimiento

Dissolve (-)-cis-4-acetoxy-cyclopent-2-enol (11.0 g, 77.4 mmol, prepared in example 19) in ethanol (50 mL) and treat with Raney nickel (1.1 g, previously washed with water (2×50 mL) and ethanol (2×50 mL), Ra--Ni). Charge the atmosphere with hydrogen at 50 psi (344.74 kPa) and shake the mixture. After 20 minutes, filter the solution and treat the filtrate with triethylamine (1.0 mL, 7.2 mmol). After one hour concentrate the solution under vacuum and distill the residue by Kugelrohr distillation (60°-80° C., 1 mm Hg), to provide the title compound (9.74 g, 87%) as a colorless oil.

Fuente