Reaktion #2656

Reaktionsgleichung

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

triethylamine

→

title compound

Ausbeute 87.3%

(-)-cis-3-acetoxy-cyclopentanol

Ausbeute 87.3%

Lösungsmittel

ethanol

Reaktionsbedingungen

Aufarbeitung

1. 1
   Waschenpreviously 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
   Filtrationfilter the solution
4. 4
   EinengenAfter 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)

Vorschrift

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.

Quelle