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

HRID 2226968노트

반응식

HRID 2226968 반응식
[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

참가 물질

7

반응물 4

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

생성물 1

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

시약·촉매·용매 2

HCID 962Water용매HCID 6228Dimethylformamide용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-23547bdad43946658ed2364844952d8c
출처 데이터셋
uspto-grants-1994_09
특허 번호
US05350761

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