Ethyl orthoformate → HCID 21717201, compound

HRID 1386262Notes

Reaction equation

HRID 1386262 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][C:6](=[O:11])[CH2:5]2.[CH:12](OCC)([O:16][CH2:17][CH3:18])[O:13][CH2:14][CH3:15]>>[Br:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[N:7]([CH:12]([O:16][CH2:17][CH3:18])[O:13][CH2:14][CH3:15])[C:6](=[O:11])[CH2:5]2

Participants

3

Reactant 2

HCID 31214Ethyl orthoformateHCID 6111935-Bromo-2-oxindole

Product 1

HCID 21717201HCID 21717201, compoundYield 68%

Procedure

A mixture of 5-bromooxindole (6.36 g, 30 mmol), (prepared according to J. Am. Chem. Soc. 1975, 67, 1656), and triethyl orthoformate (100 ml) was heated and stirred at reflux for 8 hours. The volatiles were removed by evaporation and the residue purified by column flash chromatography using petroleum ether/ether (7/3) as eluent. Evaporation of the solvents lead to a crystalline material which was collected, washed with a minimum of petroleum ether and dried under vacuum to give 5-bromo-1-diethoxymethyloxindole (6.43 g, 68%).

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 8 hours
  3. customThe volatiles were removed by evaporation
  4. customthe residue purified by column flash chromatography
  5. customEvaporation of the solvents
  6. customwas collected
  7. washwashed with a minimum of petroleum ether
  8. customdried under vacuum

Sources & evidence

ORD record
ord-f83e2ffb482841f69668a5ab07ec5bca
Source dataset
uspto-grants-2001_07
Patent number
US06265411B1

Reaction notes

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