반응 #216172

반응 방정식

ethyl acetate

4-bromotoluene

indole

4-bromotoluene

→

desired product

1-(4-Methylphenyl)-1H-indole-7-carboxylic acid, methyl ester

용매

pyridine

반응 조건

후처리

1. 1
   온도The mixture was heated in a bath
2. 2
   온도maintained at 130°±5° C. for a total of nine hours
3. 3
   workup.WAITDuring this period
4. 4
   온도After cooling
5. 5
   여과filtered through Celite
6. 6
   세척The filtrate was washed with water (3×50 ml), 0.5N hydrochloric acid (2×50 ml), 1.0N hydrochloric acid (50 ml) and saturated sodium hydrogen carbonate solution
7. 7
   건조The organic solution was dried over anhydrous magnesium sulfate
8. 8
   기타The remaining material was first chromatographed on silica gel
9. 9
   세척eluting with 5% ether in hexane
10. 10
    기타to give

실험 절차

The title C indole (1.001 g, 5.713 mmol, 1.0 eq.) was dissolved in pyridine (11.4 ml, 0.5M) and treated with 4-bromotoluene (1.76 ml, 22.85 mmol, 4 eq.) and copper(I) oxide (1.635 g, 11.43 mmol, 2.0 eq.). The mixture was heated in a bath maintained at 130°±5° C. for a total of nine hours. During this period, at 3, 5.5 and 7.5 hours, additional 4-bromotoluene (0.44 ml, 5.71 mmol, 1 eq.) and copper(I) oxide (409 mg, 2.85 mmol, 0.5 eq.) were added. After cooling, the mixture was diluted with ethyl acetate (~10 ml) and filtered through Celite. The filtrate was washed with water (3×50 ml), 0.5N hydrochloric acid (2×50 ml), 1.0N hydrochloric acid (50 ml) and saturated sodium hydrogen carbonate solution. The organic solution was dried over anhydrous magnesium sulfate and freed of solvent in vacuo. The remaining material was first chromatographed on silica gel, eluting with 5% ether in hexane to give a mixture of the desired product and starting material but free of the large amount of excess 4-bromotoluene. The mixture was then rechromatographed on silica gel, eluting with 3% acetone in hexane to give the title D compound (467 mg).

출처