Indoline → 2-(2,3-dihydro-1H-indol-1-yl)ethan-1-ol

HRID 2081926Notes

Reaction equation

HRID 2081926 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH2:3][CH2:2]1.C(=O)([O-])[O-].[K+].[K+].Br[CH2:17][CH2:18][OH:19]>C(#N)C>[OH:19][CH2:18][CH2:17][N:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH2:3][CH2:2]1

Participants

5

Reactant 3

HCID 10328IndolineHCID 108982-BromoethanolHCID 11430Potassium Carbonate

Product 1

HCID 232983052-(2,3-dihydro-1H-indol-1-yl)ethan-1-ol

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a stirred mixture of 24 parts of indoline and 83 parts of powdered anhydrous potassium carbonate in 150 parts of acetonitrile was added 50 parts of 2-bromoethanol. The mixture was gradually warmed to reflux and kept at reflux temperature for 8 hours. The mixture was filtered and the solvent was removed. The product was purified by column chromatography on a silica gel column. The eluents were 1:1 mixture of hexane with methylene chloride and then ethyl acetate. The product was 29 parts with a boiling point of 118° C. at 0.5 torr. Proton and carbon-13 NMR spectra were consistent with structure.

Workup

  1. temperatureThe mixture was gradually warmed
  2. temperatureto reflux
  3. temperatureat reflux temperature for 8 hours
  4. filtrationThe mixture was filtered
  5. customthe solvent was removed
  6. customThe product was purified by column chromatography on a silica gel column
  7. addition1:1 mixture of hexane with methylene chloride

Sources & evidence

ORD record
ord-c773c97d3ea24fc589d65c4cae341d43
Source dataset
uspto-grants-1993_02
Patent number
US05186865

Reaction notes

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