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

Participants

Reaction Steps

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.

Provenance & Evidence