Potassium Iodide → 2-(4'-Fluoro-4-biphenylylmethyl)-6-(2,2-dimethoxyethoxy)-1-oxo-1,2,3,4-tetrahydroisoquinoline

HRID 257070ノート

反応式

HRID 257070 の反応式
[CH3:1][O:2][CH:3]([O:17][CH3:18])[CH2:4][O:5][C:6]1[CH:7]=[C:8]2[C:13](=[CH:14][CH:15]=1)[C:12](=[O:16])[NH:11][CH2:10][CH2:9]2.[F:19][C:20]1[CH:25]=[CH:24][C:23]([C:26]2[CH:31]=[CH:30][C:29]([CH2:32]Br)=[CH:28][CH:27]=2)=[CH:22][CH:21]=1.[H-].[Na+].[I-].[K+]>CN(C=O)C.O>[F:19][C:20]1[CH:21]=[CH:22][C:23]([C:26]2[CH:31]=[CH:30][C:29]([CH2:32][N:11]3[CH2:10][CH2:9][C:8]4[C:13](=[CH:14][CH:15]=[C:6]([O:5][CH2:4][CH:3]([O:2][CH3:1])[O:17][CH3:18])[CH:7]=4)[C:12]3=[O:16])=[CH:28][CH:27]=2)=[CH:24][CH:25]=1

参加物

7

反応物 4

HCID 4875Potassium IodideHCID 24758Sodium hydrideHCID 189638634-(Bromomethyl)-4'-fluoro-1,1'-biphenylHCID 189638836-(2,2-Dimethoxyethoxy)-1-oxo-1,2,3,4-tetrahydroisoquinoline

生成物 1

HCID 189639412-(4'-Fluoro-4-biphenylylmethyl)-6-(2,2-dimethoxyethoxy)-1-oxo-1,2,3,4-tetrahydroisoquinoline

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6228Dimethylformamide溶媒

実験手順

To a solution of 6-(2,2-dimethoxyethoxy)-1-oxo-1,2,3,4-tetrahydroisoquinoline (5.79 g, 23.05 mmol) and 4'-fluoro-4-biphenylylmethyl bromide (9.16 g, 34.57 mmol), in DMF (100 ml) is added sodium hydride (1.1 g, 27.5 mmol) and a catalytic amount of potassium iodide. The reaction mixture is stirred for 2 hours at room temperature and is subsequently diluted with H2O (500 ml). The mixture is then extracted with EtOAc (2×300 ml). The combined EtOAc portions are washed with saturated NaCl solution (600 ml), dried over MgSO4, and concentrated in vacuo and washed with hexanes to yield the acetal, 2-(4'-fluoro-4-biphenylylmethyl)-6-(2,2-dimethoxyethoxy)-1-oxo-1,2,3,4-tetrahydroisoquinoline.

後処理

  1. extractionThe mixture is then extracted with EtOAc (2×300 ml)
  2. washThe combined EtOAc portions are washed with saturated NaCl solution (600 ml)
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated in vacuo
  5. washwashed with hexanes

出典と根拠

ORDレコード
ord-7564cb1984e942478228cdf43ac8475e
出典データセット
uspto-grants-1993_11
特許番号
US05260316

反応ノート

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