Acetone → 2-(1-methylindol-2-yl)propan-2-ol

Temperature

-30 °C

5.0 g of 1-methylindole was dissolved in 30 ml of anhydrous tetrahydrofuran. Thereto was dropwise added 30 ml of 1.5 M n-butyllithium hexane solution, at -30° C. in 5 minutes with stirring. The mixture was stirred at 0° C. for 30 minutes. Thereto was dropwise added 4.2 ml of acetone in 10 minutes at the same temperature, and the resulting mixture was stirred at room temperature for 10 minutes. The solvent was removed by distillation under reduced pressure. The residue was mixed with 100 ml of ethyl acetate and 50 ml of water to dissolve the residue. The organic layer was separated, washed with an aqueous saturated sodium chloride solution, and dried over anhydrous magnesium sulfate. The solvent was removed by distillation under reduced pressure. The residue was purified by column chromatography (eluant: toluene/ethyl acetate=50/1 to 20/1), followed by recrystallization from n-hexane, to obtain 3.25 g (yield: 45%) of 2-(1-hydroxy-1-methylethyl)-1-methylindole as colorless crystals.

1. stirringThe mixture was stirred at 0° C. for 30 minutes
2. customin 10 minutes
3. stirringthe resulting mixture was stirred at room temperature for 10 minutes
4. customThe solvent was removed by distillation under reduced pressure
5. additionThe residue was mixed with 100 ml of ethyl acetate and 50 ml of water
6. dissolutionto dissolve the residue
7. customThe organic layer was separated
8. washwashed with an aqueous saturated sodium chloride solution
9. dry with materialdried over anhydrous magnesium sulfate
10. customThe solvent was removed by distillation under reduced pressure
11. customThe residue was purified by column chromatography (eluant: toluene/ethyl acetate=50/1 to 20/1)
12. customfollowed by recrystallization from n-hexane

ORD record

ord-e2f21b0e8a6844d18bc58c3583a1ad7e

Source dataset

uspto-grants-1992_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05166204