Tetrahydrofuran → Ethyl 4-((3-methoxyphenyl)amino)-4-oxobutanoate

HRID 513924노트

반응식

HRID 513924 반응식
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[C:5]([NH2:9])[CH:4]=1.CCN([CH2:15][CH3:16])CC.C([CH:19]([CH2:23][C:24](Cl)=[O:25])[C:20](Cl)=[O:21])C.C1C[O:30]CC1>O.CCOC(C)=O>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([NH:9][C:24](=[O:25])[CH2:23][CH2:19][C:20]([O:21][CH2:15][CH3:16])=[O:30])[CH:6]=[CH:7][CH:8]=1

참가 물질

7

반응물 4

HCID 8028TetrahydrofuranHCID 8471TriethylamineHCID 108243-MethoxyanilineHCID 218646082-Ethylbutanedioyl dichloride

생성물 1

HCID 14946361Ethyl 4-((3-methoxyphenyl)amino)-4-oxobutanoate수율 86%

시약·촉매·용매 2

HCID 962Water용매HCID 8857Ethyl Acetate용매

실험 절차

To a solution of m-anisidine (10 g, 81.3 mmol) in THF (240 mL) was added Et3N (22 mL, 217.8 mmol) followed by ethyl succinyl chloride (11.14 g, 67.9 mmol). The reaction mixture was stirred at ambient temperature for 15 minutes. The reaction was diluted with H2O and EtOAc and the organic layer was separated. The organic layers were washed with H2O, 10% HCl (aq), sat. NaHCO3 (aq) and brine, dried over MgSO4 and concentrated under reduced pressure to give the title compound as a pale yellow solid (17.5 g, 86%). 1H NMR (400 MHz, CDCl3) δ 7.62-7.56 (m, 1H), 7.32-7.28 (m, 1H), 7.19 (t, J=8.0 Hz, 1H), 6.95 (d, J=8.2 Hz, 1H), 6.65 (dd, J=8.2, 2.0 Hz, 1H), 4.17 (d, J=7.0 Hz, 2H), 3.80 (s, 3H), 2.81-2.70 (m, 2H), 2.70-2.60 (m, 2H), 1.26 (t, J=7.2 Hz, 3H). [M+H]=252.3.

후처리

  1. customthe organic layer was separated
  2. washThe organic layers were washed with H2O, 10% HCl (aq), sat. NaHCO3 (aq) and brine
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated under reduced pressure

출처 및 근거

ORD 기록
ord-b74211bddfa04021b2f5bb74e1a7e9a2
출처 데이터셋
uspto-grants-2015_08
특허 번호
US09102674B2

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