Tetrahydrofuran → 2-(4-methoxy-benzyl)-4-[2-(2-methoxy-ethoxy)-ethoxy]-2,3-dihydro-1H-isoindole

HRID 424072ノート

反応式

HRID 424072 の反応式
[CH3:1][O:2][C:3]1[CH:28]=[CH:27][C:6]([CH2:7][N:8]2[C:16](=O)[C:15]3[C:10](=[CH:11][CH:12]=[CH:13][C:14]=3[O:18][CH2:19][CH2:20][O:21][CH2:22][CH2:23][O:24][CH3:25])[C:9]2=O)=[CH:5][CH:4]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-].C1COCC1>>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([CH2:7][N:8]2[CH2:16][C:15]3[C:10](=[CH:11][CH:12]=[CH:13][C:14]=3[O:18][CH2:19][CH2:20][O:21][CH2:22][CH2:23][O:24][CH3:25])[CH2:9]2)=[CH:27][CH:28]=1

参加物

4

反応物 3

HCID 8028TetrahydrofuranHCID 21226445Aluminium lithium hydrideHCID 592631332-(4-Methoxy-benzyl)-4-[2-(2-methoxy-ethoxy)-ethoxy]-isoindole-1,3-dione

生成物 1

HCID 592631462-(4-methoxy-benzyl)-4-[2-(2-methoxy-ethoxy)-ethoxy]-2,3-dihydro-1H-isoindole収率 98.7%

反応条件

温度
60 °C

実験手順

2-(4-Methoxy-benzyl)-4-[2-(2-methoxy-ethoxy)-ethoxy]-isoindole-1,3-dione (149 mg, 0.38 mmol) was treated with a 1M solution of lithium aluminium hydride in THF (5 mL, 5 mmol). The mixture was maintained at r.t. for 4 hours, 60° C. for 1 hour, then r.t. for a further 18 hours. The mixture was then cooled in ice and quenched by the dropwise addition of water (0.2 mL), 2N sodium hydroxide solution (0.4 mL) and water (0.4 mL). Magnesium sulfate was added, followed by ethyl acetate and then the mixture was stirred at r.t. for 15 minutes. The solids were removed by filtration, being well washed with ethyl acetate. Concentration of the filtrate gave a residue which was absorbed onto an SCX cartridge and washed with 5% methanol/dichloromethane then eluted with 10% IM ammonia in methanol/dichloromethane to afford the title compound (134 mg, 97%). 1H NMR (methanol-d4) 7.43-7.39 (2H, m), 7.27 (1H, t), 6.99-6.96 (2H, m), 6.90 (1H, d), 6.88 (1H, d), 4.33 (2H, s), 4.28 (2H, s), 4.23 (2H, s), 4.18-4.15 (2H, m), 3.85-3.79 (5H, m), 3.67-3.64 (2H, m), 3.54-3.51 (2H, m), 3.33 (3H, s). MS: [M+H]+ 358.

後処理

  1. temperatureThe mixture was then cooled in ice
  2. customquenched by the dropwise addition of water (0.2 mL), 2N sodium hydroxide solution (0.4 mL) and water (0.4 mL)
  3. additionMagnesium sulfate was added
  4. customThe solids were removed by filtration
  5. washbeing well washed with ethyl acetate
  6. customConcentration of the filtrate gave a residue which
  7. customwas absorbed onto an SCX cartridge
  8. washwashed with 5% methanol/dichloromethane
  9. washthen eluted with 10% IM ammonia in methanol/dichloromethane

出典と根拠

ORDレコード
ord-6da5684c6876446889545753e1553b71
出典データセット
uspto-grants-2012_01
特許番号
US08101648B2

反応ノート

読み込み中…