تفاعل #685028

معادلة التفاعل

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

المردود 19.0%

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

المردود 19.0%

المذيبات

water

ethyl acetate

ظروف التفاعل

المعالجة

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

الإجراء التجريبي

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.

المصدر