Tetrahydrofuran → HCID 67353855, 화합물

HRID 75835노트

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HRID 75835 반응식
[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

참가 물질

7

반응물 3

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

생성물 1

HCID 67353855HCID 67353855, 화합물수율 18.4%

시약·촉매·용매 3

HCID 23925Iron촉매HCID 702Ethanol용매HCID 962Water용매2회

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온도
80 °C

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-f05c31a21ef64ca2bb9cee0f6b41103d
출처 데이터셋
uspto-grants-2014_09
특허 번호
US08835428B2

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