تفاعل #2056148

معادلة التفاعل

Acetaldehyde

trans-N-(4-tert-butyldimethylsilyloxycyclohexyl)phthalimide

trans-N-(4-tert-Butyldimethylsilyloxycyclohexyl)phthalimide

bismuth tribromide

triethylsilane

→

title compound

المردود 42.7%

trans-N-(4-Ethoxycyclohexyl)phthalimide

المردود 42.7%

المذيبات

acetonitrile

acetonitrile

ظروف التفاعل

المعالجة

1. 1
   ترشيحThe mixture was filtered
2. 2
   أخرىThe filtrate was evaporated
3. 3
   workup.ADDITIONtreated with hexane

الإجراء التجريبي

Acetaldehyde (10 mL; 0.17 mol) in acetonitrile (50 mL) was added over 30 minutes to a solution of trans-N-(4-tert-butyldimethylsilyloxycyclohexyl)phthalimide (D63; 50.0 g; 0.14 mol), bismuth tribromide (6.7 g; 0.015 mol) and triethylsilane (27 mL; 0.18 mol) in acetonitrile (500 mL) stirred at ice bath temperature and the mixture was allowed to warm to room temperature overnight. The mixture was filtered and the resulting grey solid and filtrate were worked up separately. The filtrate was evaporated and treated with hexane to give the title compound as a white solid (16.35 g). The grey solid was washed with dichloromethane, the dichloromethane extract was evaporated and the residue was stirred with hexane (200 mL) to give a second crop of the title compound as a white solid (17.47 g).

المصدر