反应详情

A solution of 4-(5-nitroindol-3-ylmethyl)-3-methoxybenzoic acid (0.6 g.) in N,N-dimethylformamide (DMF), (3 ml.) was added to a stirred suspension of oil-free sodium hydride (0.088 g.) in DMF (8 ml.) under a nitrogen atmosphere at ambient temperature. The red solution was stirred for 20 minutes, and acetic anhydride (0.187 g.) added. After 1 hour, the mixture was poured into hydrochloric acid (1N, 30 ml.), extracted with ethyl acetate (3×50 ml), the combined extracts washed with water (2×20 ml.), brine, dried (MgSO4) and evaporated. The product was crystallized from a mixture of tetrahydrofuran and ether to give 4-(1-acetyl-5-nitroindol-3-ylmethyl)-3-methoxybenzoic acid (0.455 g., 67%) as a yellow powder; partial NMR (250 MHz, DMSO-d6): 2.68(s,3H, NCOCH3); 3.95(s,3H, OMe); 4.13(s,2H, ArCHhd 3).

1. waitAfter 1 hour
2. extractionextracted with ethyl acetate (3×50 ml)
3. washthe combined extracts washed with water (2×20 ml.), brine
4. dry with materialdried (MgSO4)
5. customevaporated
6. customThe product was crystallized from a mixture of tetrahydrofuran and ether