تفاعل #44022

معادلة التفاعل

Ethyl 1-(4-chlorophenylsulfonyl)-6-ethyl-4-oxopiperidine-2-carboxylate

ethyl 1-(4-chlorophenylsulfonyl)-6-ethyl-4-oxopiperidine-2-carboxylate

TMSCl

ethylene glycol

→

mixture

المردود 96.0%

ethyl 8-(4-chlorophenylsulfonyl)-9-ethyl-1,4-dioxa-8-azaspiro[4.5]decane-7-carboxylate

المردود 96.0%

المذيبات

CH2Cl2

ظروف التفاعل

المعالجة

1. 1
   درجة الحرارةrefluxed under nitrogen for 3 hours
2. 2
   تركيزThe reaction mixture was concentrated tinder reduced pressure
3. 3
   غسيلThe aqueous layer was washed with several more portions of EtOAc
4. 4
   تجفيفdried over Na2SO4
5. 5
   تركيزconcentrated

الإجراء التجريبي

Ethyl 1-(4-chlorophenylsulfonyl)-6-ethyl-4-oxopiperidine-2-carboxylate (109; 5.31 g, 14.2 mmol), TMSCl (5.41 ml, 42.6 mmol), and ethylene glycol (3.96 ml, 71.0 mmol) were added to CH2Cl2 (50 ml) and refluxed under nitrogen for 3 hours. The reaction mixture was concentrated tinder reduced pressure, and taken up in equal portions of EtOAc and water. The aqueous layer was washed with several more portions of EtOAc, dried over Na2SO4, and concentrated to give 5.67 g (96%) of a mixture of cis/trans (4:96) isomers as a clear oil which solidified upon standing. The material was used without further purification.

المصدر