Potassium Iodide → 2-(4-Methoxy-benzyl)-4-[2-(2-methoxy-ethoxy)-ethoxy]-isoindole-1,3-dione

HRID 425169

反応式

HRID 425169 の反応式
Br[CH2:2][CH2:3][O:4][CH2:5][CH2:6][O:7][CH3:8].[OH:9][C:10]1[CH:18]=[CH:17][CH:16]=[C:15]2[C:11]=1[C:12](=[O:29])[N:13]([CH2:20][C:21]1[CH:26]=[CH:25][C:24]([O:27][CH3:28])=[CH:23][CH:22]=1)[C:14]2=[O:19].C(=O)([O-])[O-].[K+].[K+].[I-].[K+]>CN(C=O)C>[CH3:28][O:27][C:24]1[CH:25]=[CH:26][C:21]([CH2:20][N:13]2[C:12](=[O:29])[C:11]3[C:15](=[CH:16][CH:17]=[CH:18][C:10]=3[O:9][CH2:2][CH2:3][O:4][CH2:5][CH2:6][O:7][CH3:8])[C:14]2=[O:19])=[CH:22][CH:23]=1

参加物

6

反応物 4

HCID 4875Potassium IodideHCID 11430Potassium CarbonateHCID 1235321-Bromo-3,6-dioxaheptane2 回HCID 592631454-Hydroxy-2-(4-methoxy-benzyl)-isoindole-1,3-dione

生成物 1

HCID 592631332-(4-Methoxy-benzyl)-4-[2-(2-methoxy-ethoxy)-ethoxy]-isoindole-1,3-dione収率 73%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
60 °C

実験手順

1-(2-Bromo-ethoxy)-2-methoxy-ethane (107 mg, 0.58 mmol) was added to a suspension of 4-hydroxy-2-(4-methoxy-benzyl)-isoindole-1,3-dione (150 mg, 0.53 mmol) and potassium carbonate (200 mg, 1.4 mmol) in DMF (2 mL). After 3.5 hours, a catalytic amount of potassium iodide was added. After a further 17 hours, the mixture was warmed to 60° C. After 3 hours, an additional amount of 1-(2-bromo-ethoxy)-2-methoxy-ethane (20 mg, 0.11 mmol) was added and the mixture maintained at 60° C. for a further 20 hours. The mixture was concentrated in vacuo then the residue was taken up in ethyl acetate and washed with potassium carbonate solution and brine. The organic phase was dried (MgSO4) and concentrated to give the title compound as a yellow oil (149 mg, 73%). 1H NMR (methanol-d4) 7.71 (1H, t), 7.43-7.40 (2H, m), 7.31-7.27 (2H, m), 6.87-6.83 (2H, m), 4.71 (2H, s), 4.37-4.34 (2H, m), 3.92-3.89 (2H, m), 3.77-3.74 (5H, m), 3.55-3.53 (2H, m), 3.33 (3H, s). MS: [M+H]+ 386.

後処理

  1. waitAfter a further 17 hours
  2. waitAfter 3 hours
  3. temperaturethe mixture maintained at 60° C. for a further 20 hours
  4. concentrationThe mixture was concentrated in vacuo
  5. washwashed with potassium carbonate solution and brine
  6. dry with materialThe organic phase was dried (MgSO4)
  7. concentrationconcentrated

出典と根拠

ORDレコード
ord-cf8f2dd6ceab4784b6978c3b6de9ce31
出典データセット
uspto-grants-2012_01
特許番号
US08106057B2

関連ノート

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