반응 #344793

반응 방정식

trans-4,5-dibenzyloxy-β-pyrrolidino-2-nitrostyrene

hydrogen

acetic anhydride

dimethylaminopyridine

3,4-dihydroxytoluene

→

5,6-diacetoxyindole

용매

triethylamine

ethyl acetate

ethyl acetate

반응 조건

후처리

1. 1
   기타The catalyst was removed over a layer of Celite
2. 2
   기타the filtrate was evaporated
3. 3
   기타to give an oily residue to which
4. 4
   기타crushed ice
5. 5
   workup.ADDITIONwas added
6. 6
   여과The resulting white precipitate was collected by filtration
7. 7
   기타to give 6.08 g (65%) of DAI

실험 절차

A suspension of 17.2 g of trans-4,5-dibenzyloxy-β-pyrrolidino-2-nitrostyrene (prepared from 3,4-dihydroxytoluene by a modified procedure of U.S. Pat. No. 3,732,245) and 3.4 g of 10% Pd/C catalyst in 200 ml ethyl acetate was shaken at room temperature, under hydrogen atmosphere and at 50 psi, for 5 hours. To this reaction mixture was added a solution of ethyl acetate (100 ml) containing acetic anhydride (24 ml), triethylamine (20 ml) and dimethylaminopyridine (800 mg) which was previously saturated with hydrogen. The resultant mixture was stirred for 30 minutes at room temperature. The catalyst was removed over a layer of Celite and the filtrate was evaporated to give an oily residue to which crushed ice was added. The resulting white precipitate was collected by filtration to give 6.08 g (65%) of DAI: mp 130°-131° C.; HNMR (300 MHz, DMSO-d6)δ 2.24 (s,6H), 6.42 (s,1H), 7.22 (s,1H), 7.32 (s,1H), 7.39 (m, 1H) 11.22 (s,1H).

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