Tetrahydrofuran → HCID 67353855、化合物

HRID 75835ノート

反応式

HRID 75835 の反応式
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([C:10]2[CH:14]=[C:13]([C:15]([NH:17][C:18](=[CH2:23])[C:19]([O:21][CH3:22])=[O:20])=[O:16])[O:12][N:11]=2)=[CH:6][CH:5]=1)([O-])=O.C1COCC1.[Cl-].[NH4+]>CCO.O.[Fe]>[NH2:1][C:4]1[CH:9]=[CH:8][C:7]([C:10]2[CH:14]=[C:13]([C:15]([NH:17][C:18](=[CH2:23])[C:19]([O:21][CH3:22])=[O:20])=[O:16])[O:12][N:11]=2)=[CH:6][CH:5]=1

参加物

7

反応物 3

HCID 8028TetrahydrofuranHCID 25517Ammonium ChlorideHCID 67355652Methyl 2-(3-(4-nitrophenyl)isoxazole-5-carboxamido)acrylate

生成物 1

HCID 67353855HCID 67353855、化合物収率 18.4%

試薬・触媒・溶媒 3

HCID 23925Iron触媒HCID 702Ethanol溶媒HCID 962Water溶媒2 回

反応条件

温度
80 °C

実験手順

Methyl 2-(3-(4-nitrophenyl)isoxazole-5-carboxamido)acrylate (1.2 g, 3.78) was dissolved in EtOH (20 ml), THF (8 ml) and water (8 ml). Then ammonium chloride (601 mg, 11.34 mmol)) and iron (529 mg, 9.45) were added and refluxed at 80° C. for 1.5 hours. Reaction mixture was cooled and filtered through celite and solvent was removed under reduced pressure to get dark brown residue. Residue was taken in water and extracted with EtOAc. The organic layer was separated, dried over Na2SO4 and concentrated to get dark brown residue, which was purified by column chromatography using EtOAc and petroleum ether to yield 200 mg (18%) of the title compound. MS: ES (+): m/z 288 (M+1); 1HNMR (DMSO-d6, 300 MHz) δ: 10.115 (s, 1H), 7.577 (d, 2H), 7.558 (s, 1H), 6.640 (d, 2H), 6.011 (s, 1H), 5.873 (s, 1H), 5.642 (s, 2H), 3.753 (s, 3H).

後処理

  1. customReaction mixture
  2. temperaturewas cooled
  3. filtrationfiltered through celite and solvent
  4. customwas removed under reduced pressure
  5. customto get dark brown residue
  6. extractionextracted with EtOAc
  7. customThe organic layer was separated
  8. dry with materialdried over Na2SO4
  9. concentrationconcentrated
  10. customto get dark brown residue, which
  11. customwas purified by column chromatography

出典と根拠

ORDレコード
ord-f05c31a21ef64ca2bb9cee0f6b41103d
出典データセット
uspto-grants-2014_09
特許番号
US08835428B2

反応ノート

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