4-Aminophenol → (E)-N-(4-hydroxyphenyl)-2-(4-(methoxymethoxy)phenyl)-3-phenylpent-2-enamide

HRID 884055ノート

反応式

HRID 884055 の反応式
[CH3:1][O:2][CH2:3][O:4][C:5]1[CH:10]=[CH:9][C:8](/[C:11](=[C:15](\[C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)/[CH2:16][CH3:17])/[C:12](O)=[O:13])=[CH:7][CH:6]=1.[NH2:24][C:25]1[CH:30]=[CH:29][C:28]([OH:31])=[CH:27][CH:26]=1.C(N(CC)C(C)C)(C)C>CN(C)C1C=CN=CC=1.C(Cl)Cl>[OH:31][C:28]1[CH:29]=[CH:30][C:25]([NH:24][C:12](=[O:13])/[C:11](/[C:8]2[CH:7]=[CH:6][C:5]([O:4][CH2:3][O:2][CH3:1])=[CH:10][CH:9]=2)=[C:15](/[C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)\[CH2:16][CH3:17])=[CH:26][CH:27]=1

参加物

6

反応物 3

HCID 4034-AminophenolHCID 81531DiisopropylethylamineHCID 57693045(E)-2-(4-(methoxymethoxy)phenyl)-3-phenylpent-2-enoic acid

生成物 1

HCID 68732343(E)-N-(4-hydroxyphenyl)-2-(4-(methoxymethoxy)phenyl)-3-phenylpent-2-enamide収率 68%

試薬・触媒・溶媒 2

HCID 142844-(Dimethylamino)pyridine触媒HCID 6344Dichloromethane溶媒

反応条件

温度
0 °C

実験手順

To a mixture of 3 (60 mg, 0.192 mmol), 4-aminophenol (23.0 mg, 0.211 mmol), 4-Dimethylaminopyridine (1.2 mg, 0.00982 mmol) and N,N-Diisopropylethylamine (37.2 mg, 0.287 mmol) in CH2Cl2 (2 ml) was added O-Benzotriazoyl-N,N,N′,N′-tetramethyluronium Hexafluorophosphate (76.5 mg, 0.202 mmol) under ice cooling, and the mixture was stirred at 0° C. for 5 min, and at room temperature for 15 h. The reaction was quenched with saturated aqueous NaHCO3 under ice cooling, and the whole was extracted with CHCl3, the organic layer was washed with brine, dried over Na2SO4, and then concentrated. Purification by silica gel flash column chromatography (eluent: hexane/AcOEt, 3:1 to 2:1) gave 6a (68%). 6a: colorless powder; 1H-NMR (CDCl3) δ 1.05 (3H, t, J=7.5 Hz), 2.77 (2H, t, J=7.5 Hz), 3.43 (3H, s), 5.09 (2H, s), 6.79 (4H, m), 7.00 (2H, d, J=8.8 Hz), 7.00 (1H, brs), 7.07 (2H, m), 7.15-7.22 (3H, m), 7.37 (2H, d, J=8.8 Hz).

後処理

  1. waitat room temperature for 15 h
  2. customThe reaction was quenched with saturated aqueous NaHCO3 under ice cooling
  3. extractionthe whole was extracted with CHCl3
  4. washthe organic layer was washed with brine
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated
  7. customPurification by silica gel flash column chromatography (eluent: hexane/AcOEt, 3:1 to 2:1)

出典と根拠

ORDレコード
ord-897125f21db14a7caaf0602529f38c13
出典データセット
uspto-grants-2012_08
特許番号
US08236987B2

反応ノート

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