反应详情

温度

70 °C

A methanol solution of 1-(1,1-dimethylethyl)2-ethyl 5-[(2-{[(1,1-dimethylethyl)(dimethyl)silyl]oxy}ethyl)oxy]-1H-indole-1,2-dicarboxylate (0.200 g, 0.431 mmol) was treated with 1 N LiOH (4 mL). A precipitate formed and THF was added to redissolve the material. The reaction was heated to 70° C. until the starting material was consumed, partitioned between EtOAc and water and the layers separated. The basic aqueous layer was acidified with conc. HCl and extracted with EtOAc. Purification was accomplished by silica gel column chromatography (0-100% EtOAc/hexanes, striped with MeOH) to afford the title compound (0.015 g, 16%) and 5-[(2-{[(1,1-dimethylethyl)(dimethyl)silyl]oxy}ethyl)oxy]-1H-indole-2-carboxylic acid (0.0114 g, 7%) 1H NMR (400 MHz, Acetone-d6) δ ppm 10.73 (br. s., 1H), 7.43 (d, 1H), 7.15 (d, 1H), 7.10 (d, 1H), 6.96 (dd, 1H), 4.07 (t, 2H), 3.88 (t, 2H).

1. customA precipitate formed
2. dissolutionto redissolve the material
3. customwas consumed
4. custompartitioned between EtOAc and water
5. customthe layers separated
6. extractionextracted with EtOAc
7. customPurification