반응 #44022

반응 방정식

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

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

TMSCl

ethylene glycol

→

mixture

수율 96.0%

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

수율 96.0%

용매

CH2Cl2

반응 조건

후처리

1. 1
   온도refluxed under nitrogen for 3 hours
2. 2
   농축The reaction mixture was concentrated tinder reduced pressure
3. 3
   세척The aqueous layer was washed with several more portions of EtOAc
4. 4
   건조dried over Na2SO4
5. 5
   농축concentrated

실험 절차

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.

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