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Methyl Salicylate → Methyl 2-[3-(quinolin-2-ylmethoxy)-benzyloxy]-benzoate

HRID 892184
ノート
印刷プレビュー

反応式

HRID 892184 の反応式
Cl.Cl[CH2:3][C:4]1[CH:5]=[C:6]([CH:19]=[CH:20][CH:21]=1)[O:7][CH2:8][C:9]1[CH:18]=[CH:17][C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[N:10]=1.C(=O)(O)[O-].[Na+].[C:27]([O:36][CH3:37])(=[O:35])[C:28]1[C:29](=[CH:31][CH:32]=[CH:33][CH:34]=1)[OH:30].[H-].[Na+].[Cl-].[NH4+]>CN(C=O)C.C(OCC)(=O)C.C(OCC)C>[N:10]1[C:11]2[C:16](=[CH:15][CH:14]=[CH:13][CH:12]=2)[CH:17]=[CH:18][C:9]=1[CH2:8][O:7][C:6]1[CH:5]=[C:4]([CH:21]=[CH:20][CH:19]=1)[CH2:3][O:30][C:29]1[CH:31]=[CH:32][CH:33]=[CH:34][C:28]=1[C:27]([O:36][CH3:37])=[O:35]
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

9

反応物 5

HCID 4133Methyl SalicylateHCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 516892Sodium BicarbonateHCID 145017072-(3-Chloromethylphenoxymethyl)quinoline hydrochloride

生成物 1

HCID 22241562Methyl 2-[3-(quinolin-2-ylmethoxy)-benzyloxy]-benzoate

試薬・触媒・溶媒 3

HCID 3283Diethyl Ether溶媒HCID 6228Dimethylformamide溶媒HCID 8857Ethyl Acetate溶媒

反応条件

温度
60 °C

実験手順

The free base of 2-(3-chloromethyl-phenoxymethyl)-quinoline hydrochloride (540 mg, 1.7 mmol, example 49) is prepard by partioning the material between ethyl ether and sodium bicarbonate and drying the organic phase with magnesium sulfate. This material is then dissolved with methyl salicylate (260 mg, 1.7 mmol) in DMF (10 mL) at 0° C. and sodium hydride (60%, 65 mg 1.7 mmol) is added. The reaction is brought to room temperature for 15 min. and is then heated at 60° C. for 6 h. The reaction is cooled and partioned between ethyl acetate and a saturated ammonium chloride solution. The organic phase is dried over magnesium sulfate, filtered, concentrated in vacuo and purified by column chromatography (silica, 50 to 80% ether in hexanes) to provide the title compound; MS (ESI) 400 (M+H)+.

後処理

  1. dry with materialdrying the organic phase with magnesium sulfate
  2. temperatureThe reaction is cooled
  3. dry with materialThe organic phase is dried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. custompurified by column chromatography (silica, 50 to 80% ether in hexanes)

出典と根拠

ORDレコード
ord-d86e556c67334af399d111d12cb61b34
出典データセット
uspto-grants-2006_02
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07005440B1

反応ノート

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