Hydrochloric Acid → 2,3-Dihydro-3-(2-methoxyethyl)-1H-indole

Participants

Reaction Conditions

Reaction Steps

Under a nitrogen atmosphere 12.6 mL (12.6 mmol) of a 1M borane in THF solution was added dropwise to 1.2 g (6.3 mmol) 3-(2-methoxy-ethyl)-1,3-dihydro-indol-2-one in 50 mL THF. The reaction mixture was refluxed for 3 h, cooled to 0° C. and combined with 10 mL methanol and then with 15 mL semi-concentrated hydrochloric acid solution. The reaction mixture was refluxed for 3 h with stirring, cooled and washed twice with ethyl acetate. The aqueous phase was made alkaline with an aqueous 4M sodium hydroxide solution and extracted three times with ethyl acetate. The organic phases were combined, dried on sodium sulphate and evaporated down.

Provenance & Evidence