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

HRID 892166ノート

反応式

HRID 892166 の反応式
[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]

参加物

6

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 67553Tetrabutylammonium Iodide触媒HCID 180Acetone溶媒

実験手順

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)+.

後処理

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

出典と根拠

ORDレコード
ord-c8707e5628f84cdfaff56bb4111b810f
出典データセット
uspto-grants-2006_02
特許番号
US07005440B1

反応ノート

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