تفاعل #2481090

معادلة التفاعل

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

hydrogen

→

title compound

المردود 92.0%

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

المردود 92.0%

المذيبات

methanol

methanol

ظروف التفاعل

المعالجة

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

الإجراء التجريبي

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%).

المصدر