반응 #54649

반응 방정식

N-(5,6,7,8-tetrahydro-8-hydroxy-4H-cyclohepta[b]thien-4-yl)acetamide

KOH

→

title compound

trans-5,6,7,8-tetrahydro-8-hydroxy-4H-cyclohepta[b]thiophen-4-amine

용매

water

water ethylene glycol

반응 조건

후처리

1. 1
   온도The mixture is heated
2. 2
   온도at reflux under nitrogen atmosphere
3. 3
   온도The mixture is cooled
4. 4
   추출extracted exhaustively with CHCl3
5. 5
   추출The chloroform extract
6. 6
   workup.ADDITIONis added to an equal volume of water
7. 7
   추출The mixture is then extracted with CHCl3
8. 8
   추출The alkaline solution is then extracted with CHCl3 exhaustively
9. 9
   건조the extracts are dried over MgSO4
10. 10
    기타evaporated to dryness

실험 절차

A sample of a cis/trans mixture of N-(5,6,7,8-tetrahydro-8-hydroxy-4H-cyclohepta[b]thien-4-yl)acetamide is added to 2 equivalents of KOH in water/ethylene glycol mixture. The mixture is heated at reflux under nitrogen atmosphere until starting material is no longer detectable by thin-layer chromatography. The mixture is cooled, diluted with water and extracted exhaustively with CHCl3. The chloroform extract is added to an equal volume of water and acidified with hydrochloric acid until the mixture is at pH 2. The mixture is then extracted with CHCl3 and then the remaining aqueous solution is made alkaline with NaOH solution. The alkaline solution is then extracted with CHCl3 exhaustively and the extracts are dried over MgSO4 and evaporated to dryness to afford the title compound.

출처