反应 #2487472

反应方程式

tert-butyl[2-(2-hydroxy-3-methylpentyl)-4-methoxyphenyl]carbamate

trifluoroacetic acid

→

title compound

收率 87.7%

2-(Butan-2-yl)-5-methoxy-1H-indole

收率 87.7%

溶剂

dichloromethane

反应条件

后处理

1. 1
   温度cooling
2. 2
   浓缩The reaction mixture was concentrated under reduced pressure
3. 3
   workup.ADDITIONTo the residue were added ethyl acetate and saturated aqueous sodium hydrogen carbonate solution
4. 4
   其他to separate the organic layer
5. 5
   洗涤The organic layer was washed with water and saturated brine successively
6. 6
   干燥dried over anhydrous sodium sulfate
7. 7
   浓缩concentrated under reduced pressure
8. 8
   workup.DISSOLUTIONUnder an argon atmosphere, the residue was dissolved in N,N-dimethylformamide (30 mL)
9. 9
   workup.ADDITION2-bromomesitylene (1.50 mL), tetrakis(triphenylphosphine) palladium(0) (472 mg), and potassium carbonate (2.25 g) were added
10. 10
    workup.STIRRINGThe mixture was stirred overnight at 150° C
11. 11
    温度The reaction mixture was cooled to room temperature
12. 12
    workup.ADDITIONwater was added
13. 13
    萃取followed by extraction with ethyl acetate
14. 14
    洗涤The organic layer was washed with water and saturated brine successively
15. 15
    干燥dried over anhydrous magnesium sulfate
16. 16
    浓缩concentrated under reduced pressure
17. 17
    其他The residue was purified by silica gel column chromatography (eluting solvent: ethyl acetate-hexane)

实验过程

To a solution of tert-butyl[2-(2-hydroxy-3-methylpentyl)-4-methoxyphenyl]carbamate (2.65 g) in dichloromethane (25 mL) was added trifluoroacetic acid (5 mL) under ice-cooling. This mixture was stirred at room temperature for 2 hours. The reaction mixture was concentrated under reduced pressure. To the residue were added ethyl acetate and saturated aqueous sodium hydrogen carbonate solution to separate the organic layer. The organic layer was washed with water and saturated brine successively, dried over anhydrous sodium sulfate, and then concentrated under reduced pressure. Under an argon atmosphere, the residue was dissolved in N,N-dimethylformamide (30 mL), and then 2-bromomesitylene (1.50 mL), tetrakis(triphenylphosphine) palladium(0) (472 mg), and potassium carbonate (2.25 g) were added thereto. The mixture was stirred overnight at 150° C. The reaction mixture was cooled to room temperature, and then water was added thereto, followed by extraction with ethyl acetate. The organic layer was washed with water and saturated brine successively, dried over anhydrous magnesium sulfate, and then concentrated under reduced pressure. The residue was purified by silica gel column chromatography (eluting solvent: ethyl acetate-hexane) to obtain the title compound (1.46 g). 1H-NMR (CDCl3) δ ppm: 0.91 (3H, t, J=7.4 Hz), 1.32 (3H, d, J=7.0 Hz), 1.55-1.80 (2H, m), 2.75-2.90 (1H, m), 3.84 (3H, s), 6.15-6.20 (1H, m), 6.77 (1H, dd, J=2.4, 8.8 Hz), 7.02 (1H, d, J=2.4 Hz), 7.19 (1H, d, J=8.8 Hz), 7.77 (1H, br s).

来源