반응 #44849

반응 방정식

12

Benzyl 4-[di(ethoxycarbonyl)methoxy]indole-1-carboxylate

hydrogen

→

8

수율 82.0%

Diethyl 2-(indol-4-yloxy)malonate

수율 82.0%

용매

ethanol

반응 조건

후처리

1. 1
   여과The catalyst was filtered off through a Celite bed
2. 2
   세척washed with ethanol
3. 3
   기타the filtrate was evaporated
4. 4
   기타to give a brown oil
5. 5
   여과Filtration through flash silica with ethyl acetate-hexanes (3:2) as eluent
6. 6
   기타followed by trituration with diethyl ether-hexanes at −20° C.

실험 절차

A solution of 12 (8.51 g, 20 mmol) in ethanol (250 mL) was mixed with 10% palladium on carbon (1.5 g) and hydrogenated at atmospheric pressure for 1 h until hydrogen uptake ceased. The catalyst was filtered off through a Celite bed and washed with ethanol, and the filtrate was evaporated to give a brown oil. Filtration through flash silica with ethyl acetate-hexanes (3:2) as eluent, followed by trituration with diethyl ether-hexanes at −20° C. gave 8 as white crystals (4.78 g, 82%), mp 52-53° C. (from diethyl ether-hexanes), identical to the material described above.

출처