Ethyl orthoformate → HCID 21717300, compound

HRID 1386265Notes

Reaction equation

HRID 1386265 reaction equation
[F: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]>>[F: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 37310125-fluoro-1,3-dihydro-2H-indol-2-one

Product 1

HCID 21717300HCID 21717300, compoundYield 40%

Procedure

A solution of 5-fluorooxindole (980 mg, 6.5 mmol), (prepared according to Synthesis 1993, 51), in triethyl orthoformate (25 ml) was stirred and heated at reflux for 8 hours. The volatiles were removed by evaporation and the crude product purified by flash chromatography using petroleum ether/ether 7/3 as eluent to give 5-fluoro-1-diethoxymethyloxindole (637 mg, 40%).

Workup

  1. temperatureheated
  2. temperatureat reflux for 8 hours
  3. customThe volatiles were removed by evaporation
  4. customthe crude product purified by flash chromatography

Sources & evidence

ORD record
ord-074e3d1fdeea43e181392dfd85fa6db7
Source dataset
uspto-grants-2001_07
Patent number
US06265411B1

Reaction notes

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