Acrylic Acid → 3-(6-Fluoroindolyl)propionic acid

反応式

[F:1][C:2]1[CH:10]=[C:9]2[C:5]([CH:6]=[CH:7][NH:8]2)=[CH:4][CH:3]=1.[C:11]([OH:15])(=[O:14])[CH:12]=[CH2:13].C(OC(=O)C)(=O)C>C(O)(=O)C>[F:1][C:2]1[CH:10]=[C:9]2[C:5]([CH:6]=[C:7]([CH2:13][CH2:12][C:11]([OH:15])=[O:14])[NH:8]2)=[CH:4][CH:3]=1

参加物

反応条件

温度: 20 °C

実験手順

The solution of 6-fluoroindol (300 mg, 2.22 mmol), acrylic acid (352 mg, 4.88 mmol) and acetic anhydride (453 mg, 4.44 mmol) in acetic acid (1.1 mL) was heated at 90° C. for 15 h. The reaction mixture was cooled to 20° C. then concentrated in vacuo. The residue was dissolved in 3N NaOH. The solution was filtered to remove insoluble material and the filtrate was acidified with conc. HCl and extracted with CHCl3. The organic solution was dried over MgSO4, filtered and concentrated in vacuo to give 3-(6-fluoroindolyl)propionic acid (240 mg, 52%) as a yellow solid.