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

HRID 513924ノート

反応式

HRID 513924 の反応式
[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

参加物

7

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 8857Ethyl Acetate溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-b74211bddfa04021b2f5bb74e1a7e9a2
出典データセット
uspto-grants-2015_08
特許番号
US09102674B2

反応ノート

読み込み中…