Iodoethane → HCID 524514, compound

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.

1. temperaturethe resulting solution was maintained at room temperature for an additional 3 hours
2. customThe reaction mixture was then quenched
3. additionby adding ethanol (100 mL)
4. extractionThe resulting solution was extracted with dichloromethane (3×500 mL)
5. concentrationconcentrated
6. customThe residue was purified by column chromatography

ORD record

ord-6fa22f081167480092f5b75b62251ad1

Source dataset

uspto-grants-2010_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07696229B2