反応 #2656

反応方程式

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

triethylamine

→

title compound

収率 87.3%

(-)-cis-3-acetoxy-cyclopentanol

収率 87.3%

溶媒

ethanol

反応条件

後処理

1. 1
   洗浄previously 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
   ろ過filter the solution
4. 4
   濃縮After 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)

実験手順

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.

出典