Potassium Carbonate → {2-[3-(Quinolin-2-ylmethoxy)phenoxymethyl]-6-methylphenoxy}acetonitrile

HRID 892166노트

반응식

HRID 892166 반응식
[N:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[CH2:11][O:12][C:13]1[CH:14]=[C:15]([OH:19])[CH:16]=[CH:17][CH:18]=1.Br[CH2:21][C:22]1[CH:31]=[CH:30][CH:29]=[C:28]([CH3:32])[C:23]=1[O:24][CH2:25][C:26]#[N:27].C(=O)([O-])[O-].[K+].[K+]>[I-].C([N+](CCCC)(CCCC)CCCC)CCC.CC(C)=O>[N:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[CH2:11][O:12][C:13]1[CH:14]=[C:15]([CH:16]=[CH:17][CH:18]=1)[O:19][CH2:21][C:22]1[CH:31]=[CH:30][CH:29]=[C:28]([CH3:32])[C:23]=1[O:24][CH2:25][C:26]#[N:27]

참가 물질

6

반응물 3

HCID 11430Potassium CarbonateHCID 10988736Phenol, 3-(2-quinolinylmethoxy)-HCID 222414892-Cyanomethoxy-3-methylbenzyl bromide

생성물 1

HCID 22241372{2-[3-(Quinolin-2-ylmethoxy)phenoxymethyl]-6-methylphenoxy}acetonitrile

시약·촉매·용매 2

HCID 67553Tetrabutylammonium Iodide촉매HCID 180Acetone용매

실험 절차

3-(Quinolin-2-ylmethoxy)-phenol (1.3 g, 5.4 mmol, example 3), (2-bromomethyl-6-methyl-phenoxy)-acetonitrile (1.56 g, 6.5 mmol, example 24), tetrabutylammonium iodide (99 mg, 0.27 mmol) and potassium carbonate (0.45 g, 3.3 mmol) are refluxed in acetone (20 mL) for 16 h. The reaction is filtered, washed with dichloromethane, concentrated and purified by column chromatography (silica, 1% ether in dichloromethane) to provide the title compound. MS (ESI) 411 (M+H)+.

후처리

  1. filtrationThe reaction is filtered
  2. washwashed with dichloromethane
  3. concentrationconcentrated
  4. custompurified by column chromatography (silica, 1% ether in dichloromethane)

출처 및 근거

ORD 기록
ord-c8707e5628f84cdfaff56bb4111b810f
출처 데이터셋
uspto-grants-2006_02
특허 번호
US07005440B1

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