반응 #161649

반응 방정식

sodium bicarbonate

N-Benzhydrylidene-N′-(3,5-di-tert-butyl-phenyl)-hydrazine

ethyl pyruvate

p-toluene sulfonic acid monohydrate

→

4,6-di-tert-butyl-1H-indole-2-carboxylic acid ethyl ester

용매

water

ethanol

반응 조건

후처리

1. 1
   온도This was heated
2. 2
   온도After cooling it to room temperature
3. 3
   추출The product was extracted into ethyl acetate
4. 4
   기타The organic layer was isolated
5. 5
   세척washed with an aqueous solution saturated with sodium chloride
6. 6
   건조dried over magnesium sulfate
7. 7
   기타The desiccant was removed by filtration, and concentration
8. 8
   기타Then, the residue obtained by concentration under reduced pressure
9. 9
   기타was purified by silica gel column chromatography (hexane/ethyl acetate=100/5)

실험 절차

N-Benzhydrylidene-N′-(3,5-di-tert-butyl-phenyl)-hydrazine (617 mg, 1.6 mmol) was dissolved in ethanol (12 ml). Then, ethyl pyruvate (212 μl, 1.9 mmol) and p-toluene sulfonic acid monohydrate (914 mg, 4.8 mmol) were added thereto. This was heated and stirred at 150° C. by microwave under a nitrogen atmosphere for one hour. After cooling it to room temperature, the reaction mixture was combined with water and an aqueous solution saturated with sodium bicarbonate. The product was extracted into ethyl acetate. The organic layer was isolated, and washed with an aqueous solution saturated with sodium chloride, and dried over magnesium sulfate. The desiccant was removed by filtration, and concentration was performed. Then, the residue obtained by concentration under reduced pressure was purified by silica gel column chromatography (hexane/ethyl acetate=100/5). Thus, 4,6-di-tert-butyl-1H-indole-2-carboxylic acid ethyl ester was obtained as a brown solid (268 mg, 56%).

출처