반응 #2487472

반응 방정식

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

trifluoroacetic acid

→

title compound

수율 87.7%

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

수율 87.7%

용매

dichloromethane

반응 조건

후처리

1. 1
   온도cooling
2. 2
   농축The 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
   기타to separate the organic layer
5. 5
   세척The organic layer was washed with water and saturated brine successively
6. 6
   건조dried over anhydrous sodium sulfate
7. 7
   농축concentrated 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
    온도The reaction mixture was cooled to room temperature
12. 12
    workup.ADDITIONwater was added
13. 13
    추출followed by extraction with ethyl acetate
14. 14
    세척The organic layer was washed with water and saturated brine successively
15. 15
    건조dried over anhydrous magnesium sulfate
16. 16
    농축concentrated under reduced pressure
17. 17
    기타The residue was purified by silica gel column chromatography (eluting solvent: ethyl acetate-hexane)

실험 절차

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).

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