Реакция #2656

Уравнение реакции

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

triethylamine

→

title compound

Выход 87.3%

(-)-cis-3-acetoxy-cyclopentanol

Выход 87.3%

Растворители

ethanol

Условия реакции

Обработка

1. 1
   Промывкаpreviously 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
   Фильтрацияfilter the solution
4. 4
   КонцентрированиеAfter 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)

Методика

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.

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