반응 #2656

반응 방정식

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

triethylamine

→

title compound

수율 87.3%

(-)-cis-3-acetoxy-cyclopentanol

수율 87.3%

용매

ethanol

반응 조건

후처리

1. 1
   세척previously 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
   여과filter the solution
4. 4
   농축After 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)

실험 절차

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.

출처