反应详情

Melatonin (126 mg) is dissolved in tetrahydrofuran (10 ml) in a 50 ml round-bottomed flask, sodium hydride (200 mg) is then added and the mixture is maintained at reflux (10 min). After cooling (0° C.), acetyl chloride is added and the mixture is kept stirring overnight (room temperature). After filtration and dilution (EtOAc), the organic phase is washed with water and then separated on a silica plate. N-[2-(1-Acetyl-5-methoxyindol-3-yl)ethyl]acetamide (1) is mainly obtained, along with a side product, N-[2-(1-acetyl-5-methoxyindol-3-yl)ethyl]diacetamide (10) (cf. Example 10).

1. temperaturethe mixture is maintained
2. temperatureat reflux (10 min)
3. additionis added
4. filtrationAfter filtration and dilution (EtOAc)
5. washthe organic phase is washed with water
6. customseparated on a silica plate