2-(2-Nitrovinyl)-5-phenylfuran → 2-Furanethanamine, 5-phenyl-
反応式
[H-].[Al+3].[Li+].[H-].[H-].[H-].[N+:7]([CH:10]=[CH:11][C:12]1[O:13][C:14]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)=[CH:15][CH:16]=1)([O-])=O>>[C:17]1([C:14]2[O:13][C:12]([CH2:11][CH2:10][NH2:7])=[CH:16][CH:15]=2)[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=1参加物
3
実験手順
Cool lithium aluminum hydride (21 mL, 1.0 M solution in ether) to 0° C. and add 2-(2-nitrovinyl)-5-phenylfuran (760 mg, 3.53 mmol in 5 mL of ether). Stir reaction to room temperature for 15 hours. Re-cool reaction to 0° C. and quench with 0.80 mL of water, followed by 0.80 mL 1M sodium hydroxide and 0.80 mL of water (×3). Dilute reaction with additional tetrahydrofuran and stir at room temperature for 2 hours. Filter and dry over sodium sulfate and filter again. Concentrate and perform flash column chromatography (methylene chloride, MeOH, NH4OH) to give 134 mg (20% yield) of the title compound as a brown oil. MH+ 188.0.
後処理
- customreaction to room temperature for 15 hours
- customRe-cool reaction to 0° C.