反応式
[CH:1]([O:4][C:5]1[CH:25]=[CH:24][CH:23]=[CH:22][C:6]=1[O:7][CH2:8][CH2:9][CH2:10][N:11]1[C:19](=O)[C:18]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)C1=O)([CH3:3])[CH3:2].C(OC1C=CC=CC=1O)(C)C.C([O-])([O-])=O.[K+].[K+].BrCCC[N:47]1[C:55](=[O:56])C2[C:49](=[CH:50][CH:51]=[CH:52]C=2)[C:48]1=O>CN(C=O)C>[CH:1]([O:4][C:5]1[CH:25]=[CH:24][CH:23]=[CH:22][C:6]=1[O:7][CH2:8][CH2:9][CH2:10][NH:11][CH2:19][C:18]1[CH:17]=[C:16]([C:55]([N:47]2[CH2:52][CH2:51][CH2:50][CH2:49][CH2:48]2)=[O:56])[CH:15]=[CH:14][CH:13]=1)([CH3:2])[CH3:3]参加物
反応物 4
生成物 1
試薬・触媒・溶媒 1
反応条件
- 温度
- 25 °C
実験手順
2-[3-(2-Isopropoxy-phenoxy)-propyl]-isoindole-1,3-dione. To a solution of 2-isopropoxy-phenol (0.50 g, 3.3 mmol) in DMF (5 mL) was added K2CO3 (2.3 g, 17 mmol), and the resulting suspension was stirred at 25° C. for 15 min. A solution of 2-(3-bromo-propyl)-isoindole-1,3-dione (0.97 g, 3.6 mmol) in DMF (2 mL) was added, and the reaction mixture was heated to 80° C. for 18 h. The mixture was filtered, and the filtrate was diluted with 1:1 Et2O/EtOAc (100 mL), washed with H2O (2×20 mL) then brine (20 mL), dried (MgSO4), filtered, and concentrated under reduced pressure. The crude residue was purified by column chromatography (5-20% EtOAc/hexanes) to provide the desired product (0.956 g, 87%). 1H NMR (400 MHz, CDCl3): 7.87-7.82 (m, 2H), 7.73-7.69 (m, 2H), 6.93-6.86 (m, 4H), 4.46 (hept, J=6.1 Hz, 1H), 4.06 (t, J=6.2 Hz, 2H), 3.92 (t, J=7.1 Hz, 2H), 2.20 (quint, J=6.4 Hz, 2H), 1.33 (d, J=6.1 Hz, 6H).
後処理
- temperaturethe reaction mixture was heated to 80° C. for 18 h
- filtrationThe mixture was filtered
- additionthe filtrate was diluted with 1:1 Et2O/EtOAc (100 mL)
- washwashed with H2O (2×20 mL)
- dry with materialbrine (20 mL), dried (MgSO4)
- filtrationfiltered
- concentrationconcentrated under reduced pressure
- customThe crude residue was purified by column chromatography (5-20% EtOAc/hexanes)
出典と根拠
- ORDレコード
- ord-3ced65519a954c72a2122f7b9194f19b
- 出典データセット
- uspto-grants-2011_03
- 特許番号
- US07915420B2
関連ノート
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