2,5-Dimethoxytetrahydrofuran → Methyl 9H-carbazole-4-carboxylate

HRID 1197173Notes

Reaction equation

HRID 1197173 reaction equation
[NH:1]1[C:9]2[CH:8]=[CH:7][CH:6]=[C:5]([C:10]([O:12][CH3:13])=[O:11])[C:4]=2[CH:3]=[CH:2]1.CO[CH:16]1[CH2:20][CH2:19][CH:18](OC)O1.O.C1(C)C=CC(S(O)(=O)=O)=CC=1>CO>[CH:8]1[C:9]2[NH:1][C:2]3[C:3](=[CH:18][CH:19]=[CH:20][CH:16]=3)[C:4]=2[C:5]([C:10]([O:12][CH3:13])=[O:11])=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 790982,5-DimethoxytetrahydrofuranHCID 521998p-Toluenesulfonic acid monohydrateHCID 2733668methyl 1H-indole-4-carboxylate

Product 1

HCID 19897888Methyl 9H-carbazole-4-carboxylateYield 13.5%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of 52.56 g of methyl indole-4-carboxylate, 51.55 g of 2,5-dimethoxytetrahydrofuran and 28.53 g of p-toluenesulfonic acid monohydrate in 300 ml of methanol was refluxed for 10 hours. Then, following a treatment similar to that of Example 1(1), there was obtained 9.14 g of methyl carbazole-4-carboxylate.

Workup

  1. temperaturewas refluxed for 10 hours

Sources & evidence

ORD record
ord-47f4add07be140218692b7213a697950
Source dataset
uspto-grants-1992_05
Patent number
US05116995

Reaction notes

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