Vinyl Acetate → Methyl 1H-indole-1-carboxylate

HRID 745313Notes

Reaction equation

HRID 745313 reaction equation
[CH3:1][O:2][C:3]([N:5](O)[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)=[O:4].[C:13](OC=C)(=O)[CH3:14]>>[CH3:1][O:2][C:3]([N:5]1[C:6]2[C:11](=[CH:10][CH:9]=[CH:8][CH:7]=2)[CH:14]=[CH:13]1)=[O:4]

Participants

3

Reactant 2

HCID 7904Vinyl AcetateHCID 9815320Carbamic acid, hydroxyphenyl-, methyl ester

Product 1

HCID 12361768Methyl 1H-indole-1-carboxylate

Procedure

A solution of 12.0 g of N-methoxycarbonyl-N-hydroxyaniline in 120 ml of vinyl acetate is stirred with 200 mg of Li2PdCl4 for 7 hours at 60° C.; it is then washed with brine, dried over magnesium sulfate and concentrated by evaporation. Chromatography through silica gel (toluene/ethyl acetate 4:1) yields 7.3 g of N-methoxycarbonylindole as colourless oil; IR spectrum (CHCl3): 1730 (CO): NMR spectrum (60 MHz, CDCl3): 1.47 (t, J=7, CH3); 4.47 (q, J=7, CH2); 6.53 (d, J=3.5, CH); 7.1-7.7 (m, 4H); 8.13 (m, 1H) ppm. 1.4 g of an O-acetylated educt in the form of yellow oil are obtained as a second fraction of chromatography.

Workup

  1. washit is then washed with brine
  2. dry with materialdried over magnesium sulfate
  3. concentrationconcentrated by evaporation

Sources & evidence

ORD record
ord-02ae0d8bedc54c9294e2ad0ee01002ba
Source dataset
uspto-grants-1986_07
Patent number
US04598156

Reaction notes

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