反应详情

To a round bottom flask equipped with a stir bar was added 4-bromomethyl-6-(2-methoxyphenyl)-2,2-dimethyl-1,2-dihydroquinoline (see Example 1) (0.36 mmol), DMF (3.6 mL), and NaN3 (0.54 mmol, 1.5 equiv). The reaction was stirred 48 hours under argon, then diluted with EtOAc and water, separated, and the aqueous phase was extracted with EtOAc. The combined organics were washed with water. The water was back-extracted with EtOAc and the combined organics were washed with brine and concentrated in vacuo. The residue was diluted with hexanes and a minimal amount of EtOAc and applied to a silica gel column. Flash chromatography, eluting with 0-30% EtOAc/hexanes provided 181 mg of 4-azidomethyl-6-(2-methoxyphenyl)-2,2-dimethyl-1,2-dihydroquinoline as a brown oil.

1. customTo a round bottom flask equipped with a stir bar
2. customseparated
3. extractionthe aqueous phase was extracted with EtOAc
4. washThe combined organics were washed with water
5. extractionThe water was back-extracted with EtOAc
6. washthe combined organics were washed with brine
7. concentrationconcentrated in vacuo
8. additionThe residue was diluted with hexanes
9. washFlash chromatography, eluting with 0-30% EtOAc/hexanes