반응 #685028

반응 방정식

NaOH

trifluoroacetic acid

3-(3-ethoxy-3-oxopropyl)-4-oxo-4,5,6,7-tetrahydro-1H-indole

3-(3-Ethoxy-3-oxopropyl)-4-oxo-4,5,6,7-tetrahydro-1H-indole

trimethylorthoformate

→

3-(3-ethoxy-3-oxopropyl)-2-formyl-4-oxo-4,5,6,7-tetrahydro-1H-indole

수율 19.0%

3-(3-Ethoxy-3-oxopropyl)-2-formyl-4-oxo-4,5,6,7-tetrahydro-1H-indole

수율 19.0%

용매

water

ethyl acetate

반응 조건

후처리

1. 1
   온도warmed up to room temperature
2. 2
   workup.STIRRINGstirred for 2.0 h
3. 3
   기타The organic layer was collected
4. 4
   세척washed with saturated aqueous NaHCO3 (200 mL)
5. 5
   건조dried over MgSO4 (s)
6. 6
   농축concentrated under reduced pressure
7. 7
   기타The oily residue was purified by gravity column chromatography (50% EtOAc in hexanes)

실험 절차

To a trifluoroacetic acid solution (47 mL) containing 3-(3-ethoxy-3-oxopropyl)-4-oxo-4,5,6,7-tetrahydro-1H-indole (4, 10.0 g, 42.5 mmol) was added with trimethylorthoformate (13.6 g, 128 mmol) at 0° C. The reaction was stirred at 0° C. for 30 min, warmed up to room temperature and stirred for 2.0 h. The solution was added with ethyl acetate (250 mL), water (200 mL) and NaOH (18 g). The organic layer was collected and washed with saturated aqueous NaHCO3 (200 mL), dried over MgSO4 (s), and concentrated under reduced pressure. The oily residue was purified by gravity column chromatography (50% EtOAc in hexanes) to give 3-(3-ethoxy-3-oxopropyl)-2-formyl-4-oxo-4,5,6,7-tetrahydro-1H-indole (5, 2.1 g, 8.0 mmol) as yellow solids in 19% yield.

출처