Reaktion #2661

Reaktionsgleichung

(+/-)-cis-4-tert-butyldimethylsilyloxy-2-cyclopentenol

hydrogen

→

title compound

Ausbeute 92.0%

(+/-)-cis-3-tert-butyldimethylsilyloxycyclopentanol

Ausbeute 92.0%

Lösungsmittel

methanol

methanol

Reaktionsbedingungen

Aufarbeitung

1. 1
   Filtrationfilter through diatomaceous earth
2. 2
   Waschenrinse the solids with methanol (50 mL)
3. 3
   EinengenConcentrate the filtrate under vacuum (15 mmHg/40° C.)
4. 4
   Sonstigepurify the residue
5. 5
   workup.DISTILLATIONby Kugelrohr distillation (0.6 mmHg/60°-65° C.)

Vorschrift

Combine (+/-)-cis-4-tert-butyldimethylsilyloxy-2-cyclopentenol (2.50 g, 11.6 mmol, prepared in example 3) and Ni2B (8.5 mL of a 0.14M slurry in methanol, 10 mol %) in methanol (14 mL). Stir the slurry under an atmosphere of hydrogen for 18.5 hours. Then replace the hydrogen atmosphere with nitrogen, filter through diatomaceous earth and rinse the solids with methanol (50 mL). Concentrate the filtrate under vacuum (15 mmHg/40° C.) and purify the residue by Kugelrohr distillation (0.6 mmHg/60°-65° C.) to provide the title compound as a colorless oil (2.31 g, 92%).

Quelle