Iodoethane → HCID 524514, compound

Participants

Reaction Steps

NaH (10 g) was added to a chilled (0° C.) solution of indoline (30 g, 252.10 mmol) in tetrahydrofuran (300 mL). The resulting solution was then stirred at room temperature for 30 minutes. Iodoethane (50 g, 322.58 mmol) was then added dropwise and the resulting solution was maintained at room temperature for an additional 3 hours. The reaction mixture was then quenched by adding ethanol (100 mL). The resulting solution was extracted with dichloromethane (3×500 mL), and the organic layers were combined and concentrated. The residue was purified by column chromatography using a 100:1 ethyl acetate/petroleum ether solvent system to give 29 g (78%) of 1-ethylindoline as yellow oil.

Provenance & Evidence