반응 #736783

반응 방정식

Oxalyl chloride

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

→

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

용매

DMF

반응 조건

후처리

1. 1
   온도cooling
2. 2
   기타the temperature below -20°
3. 3
   workup.STIRRINGStirring
4. 4
   workup.STIRRINGstirring
5. 5
   workup.WAITis continued for 2 hours at -30° to -20°
6. 6
   기타at room temperature
7. 7
   기타overnight
8. 8
   기타The mixture is evaporated to dryness
9. 9
   세척washed with sat. NaHCO3
10. 10
    건조dried (MgSO4)
11. 11
    기타evaporated to dryness to an oil which
12. 12
    기타is chromatographed on silica gel

실험 절차

Oxalyl chloride (5.2 g) is added to 200 mL of DMF dropwise under stirring and cooling keeping the temperature below -20°. Stirring is continued for 0.5 hour at the same temperature. To the mixture 7.0 g of ethyl 6-benzyloxy-4-hydroxy-6-methyl-5,6,7,8-tetrahydroquinoline-3-carboxylate is added in small portions and stirring is continued for 2 hours at -30° to -20°, then at room temperature overnight. The mixture is evaporated to dryness and the residue is taken up in CH2Cl2, washed with sat. NaHCO3, dried (MgSO4) and evaporated to dryness to an oil which is chromatographed on silica gel to yield ethyl 6-benzyloxy-4-chloro-6-methyl-5,6,7,8-tetrahydroquinoline-3-carboxylate.

출처