反应详情

To a solution of 1-methylindole-3-carboxaldehyde (10.0 g, 62.8 mmole) in MeOH (100 mL) was added a solution of 2.0 M CH3NH2 in MeOH (126 mL, 252.0 mmole). The reaction was stirred at RT for 2 hrs, then was concentrated to a light yellow oil. This oil was dissolved in EtOH (300 mL), and NaBH4 (2.38 g, 62.8 mmole) was added. After 2 hrs the reaction was concentrated to a slurry and dissolved in 1.0 N NaOH (75 mL). The aqueous solution was extracted with Et2O (2×200 mL) and the combined organic fractions were dried over Na2SO4 and concentrated. Flash chromatography on silica gel (9:1 CHCl3/MeOH containing 5% NH4OH) and drying in high vacuum left the tile compound (10.1 g, 92%) as a faintly yellow oil: MS (ES) m/e 175 (M+H)+.

1. concentrationwas concentrated to a light yellow oil
2. dissolutionThis oil was dissolved in EtOH (300 mL)
3. concentrationAfter 2 hrs the reaction was concentrated to a slurry
4. dissolutiondissolved in 1.0 N NaOH (75 mL)
5. extractionThe aqueous solution was extracted with Et2O (2×200 mL)
6. dry with materialthe combined organic fractions were dried over Na2SO4
7. concentrationconcentrated
8. customFlash chromatography on silica gel (9:1 CHCl3/MeOH containing 5% NH4OH) and drying in high vacuum
9. waitleft the tile compound (10.1 g, 92%) as a faintly yellow oil