Ethyl orthoformate → HCID 21717301, compound

HRID 1386271Notes

Reaction equation

HRID 1386271 reaction equation
[CH2:1]([O:8][C:9]1[CH:10]=[C:11]2[C:15](=[CH:16][CH:17]=1)[NH:14][C:13](=[O:18])[CH2:12]2)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH:19](OCC)([O:23][CH2:24][CH3:25])[O:20][CH2:21][CH3:22]>>[CH2:1]([O:8][C:9]1[CH:10]=[C:11]2[C:15](=[CH:16][CH:17]=1)[N:14]([CH:19]([O:23][CH2:24][CH3:25])[O:20][CH2:21][CH3:22])[C:13](=[O:18])[CH2:12]2)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

3

Reactant 2

HCID 31214Ethyl orthoformateHCID 184387465-(Benzyloxy)indolin-2-one

Product 1

HCID 21717301HCID 21717301, compoundYield 73%

Procedure

A mixture of 5-benzyloxyoxindole (1.88 g, 7.9 mmol), (EP 0636608 A1), and triethyl orthoformate (180 ml) was heated at reflux with stirring for 3 hours. The volatiles were removed by evaporation and the residue was 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 by filtration and dried under vacuum to give 5-benzyloxy-1-diethoxymethyloxindole (1.96 g, 73%).

Workup

  1. temperaturewas heated
  2. temperatureat reflux
  3. customThe volatiles were removed by evaporation
  4. customthe residue was purified by column flash chromatography
  5. customEvaporation of the solvents
  6. filtrationwas collected by filtration
  7. customdried under vacuum

Sources & evidence

ORD record
ord-bef1bdc96cf64db78b4c045c7361e7ec
Source dataset
uspto-grants-2001_07
Patent number
US06265411B1

Reaction notes

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