Tetrahydrofuran → 6-fluoro-1H-indole-5-carboxylic acid

反応式

[F:1][C:2]1[CH:10]=[C:9]2[C:5]([CH:6]=[CH:7][N:8]2[Si](C(C)C)(C(C)C)C(C)C)=[CH:4][C:3]=1[C:21]([OH:23])=[O:22].C1COCC1.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>CCOCC>[F:1][C:2]1[CH:10]=[C:9]2[C:5]([CH:6]=[CH:7][NH:8]2)=[CH:4][C:3]=1[C:21]([OH:23])=[O:22]

参加物

実験手順

6-Fluoro-1-(triisopropylsilyl)-1H-indole-5-carboxylic acid (4.36 g, 13.00 mmol) was treated with THF (30 mL) and tetra-n-butylammonium fluoride (1.0 M in THF, 13.0 mL, 13.00 mmol) and stirred at RT for 15 min. The reaction mixture was diluted with Et2O (30 mL) resulting in a suspension which was collected by filtration affording 6-fluoro-1H-indole-5-carboxylic acid (2.41 g) as a white crystalline solid. MS (ESI, pos. ion) m/z: 180.1 (M+H)+. The crude material was used in the subsequent reaction without further purification.