反应详情

Trifluoroacetic acid (1.25 g) was added slowly to a stirred solution of methyl 4-[5-(2-carboxy-1 hydroxy-2-methylpropyl)-1-propylindol-3-ylmethyl]-3-methoxybenzoate 0.5 g) and triethylsilane (0.128 g) in carbon tetrachloride (7 ml) under an atmosphere of nitrogen. After 35 min, the mixture was poured into water and extracted with ethyl acetate. The combined organic extracts were washed (water (4 times), brine), dried (MgSO4) and evaporated to give a dark oil. The product was purified by flash chromatography, eluting with 90:10:2 toluene:ethyl acetate:acetic acid, to give methyl 4-[5-(2-carboxy-2-methylpropyl)-1-propylindol-3-ylmethyl]-3-methoxybenzoate as an oil (0.27 g, 56%): partial NMR (250 MHz, DMSO-d6): 0.82(t, 3H, CH2CH3), 1.02(s, 6H, C(CH3)2), 1.68(m, 2H, CH2CH3), 291(s, 2H, C(CH3)2CH2), 3.82(s, 3H, OCH3), 3.89(s, 3H, OCH3), 4.01(m, 4H, NCH2, ArCH2Ar'), 12.15(br s, about 1H, COOH).

1. extractionextracted with ethyl acetate
2. washThe combined organic extracts were washed (water (4 times), brine)
3. dry with materialdried (MgSO4)
4. customevaporated
5. customto give a dark oil
6. customThe product was purified by flash chromatography
7. washeluting with 90:10:2 toluene