반응 #736774

반응 방정식

ethyl 4-hydroxy-6-ethyl-5,6,7,8-tetrahydroquinoline-3-carboxylate

phosphorus oxychloride

→

ethyl 4-chloro-6-ethyl-5,6,7,8-tetrahydroquinoline-3-carboxylate

반응 조건

후처리

1. 1
   온도to reflux under nitrogen for five hours
2. 2
   기타The POCl3 is removed under vacuum
3. 3
   workup.DISSOLUTIONthe residue is dissolved in CHCl3
4. 4
   세척the solution is washed with cold 2N NaOH, saturated NaCl
5. 5
   건조dried over anhydrous MgSO4
6. 6
   기타evaporated to dryness
7. 7
   기타The crude product is purified through a short column of silica gel eluting with EtOAc
8. 8
   기타Removal of solvent under vacuum

실험 절차

A solution of 3.5 g of ethyl 4-hydroxy-6-ethyl-5,6,7,8-tetrahydroquinoline-3-carboxylate in 35 ml phosphorus oxychloride is heated to reflux under nitrogen for five hours. The POCl3 is removed under vacuum, the residue is dissolved in CHCl3, and the solution is washed with cold 2N NaOH, saturated NaCl, then dried over anhydrous MgSO4, and evaporated to dryness. The crude product is purified through a short column of silica gel eluting with EtOAc. Removal of solvent under vacuum affords ethyl 4-chloro-6-ethyl-5,6,7,8-tetrahydroquinoline-3-carboxylate as an oil, which is used directly in the next step.

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