2-(2-Nitrovinyl)-5-phenylfuran → 2-Furanethanamine, 5-phenyl-

HRID 915649

反応式

HRID 915649 の反応式
[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

反応物 2

HCID 8012792-(2-Nitrovinyl)-5-phenylfuranHCID 21226445Aluminium lithium hydride

生成物 1

HCID 248382692-Furanethanamine, 5-phenyl-収率 20.3%

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

  1. customreaction to room temperature for 15 hours
  2. customRe-cool reaction to 0° C.
  3. customquench with 0.80 mL of water
  4. additionDilute
  5. customreaction with additional tetrahydrofuran
  6. stirringstir at room temperature for 2 hours
  7. filtrationFilter
  8. dry with materialdry over sodium sulfate
  9. filtrationfilter again
  10. concentrationConcentrate

出典と根拠

ORDレコード
ord-978aa5b525f84227a4dcd45260e51ec9
出典データセット
uspto-grants-2007_09
特許番号
US07265246B2

関連ノート

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