반응 #11216

반응 방정식

azidocinnamate

Methyl-2-azido-3-[4′-(benzyloxy)-3′-methoxyphenyl]prop-2-enoate

→

methyl-6-(benzyloxy)-5-methoxyindole-2-carboxylate

용매

xylene

xylene

반응 조건

후처리

1. 1
   workup.ADDITIONwas added dropwise
2. 2
   온도the reaction mixture was heated
3. 3
   온도at reflux for a further 15 min
4. 4
   기타most of the xylene was removed by distillation

실험 절차

A solution of the azidocinnamate (55) (12.2 g, 36.0 mmol) prepared as described in example 247 in xylene (300 mL) was added dropwise to refluxing xylene (100 mL) over 1.5 h, the reaction mixture was heated at reflux for a further 15 min and then most of the xylene was removed by distillation. The residue, on cooling to room temperature, formed a fine cream precipitate of methyl-6-(benzyloxy)-5-methoxyindole-2-carboxylate which was collected by filtration. The remaining xylene was removed from the mother liquor azeotropically with ethanol, the residue was recrystallized from ethanol to give further methyl-6-(benzyloxy)-5-methoxyindole-2-carboxylate. The mother liquor was again concentrated and the residue recrystallized. The methyl-6-(benzyloxy)-5-methoxyindole-2-carboxylate (56) (9.9 g total, 88%) was used in the next step without purification. Found: C, 69.38; H, 5.54; N, 4.55. C18H17NO4 requires: C, 69.44; H, 5.50; N, 4.50.

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