Potassium Carbonate → Ethyl 2-hydroxy-6-methyl-4-[3-(quinolin-2-ylmethoxy)-benzyloxy]-benzoate

HRID 892188ノート

反応式

HRID 892188 の反応式
[CH2:1]([O:3][C:4](=[O:14])[C:5]1[C:10]([CH3:11])=[CH:9][C:8]([OH:12])=[CH:7][C:6]=1[OH:13])[CH3:2].Cl.Cl[CH2:17][C:18]1[CH:19]=[C:20]([CH:33]=[CH:34][CH:35]=1)[O:21][CH2:22][C:23]1[CH:32]=[CH:31][C:30]2[C:25](=[CH:26][CH:27]=[CH:28][CH:29]=2)[N:24]=1.C(=O)([O-])[O-].[K+].[K+]>[I-].C([N+](CCCC)(CCCC)CCCC)CCC.CC(C)=O>[OH:13][C:6]1[CH:7]=[C:8]([O:12][CH2:17][C:18]2[CH:35]=[CH:34][CH:33]=[C:20]([O:21][CH2:22][C:23]3[CH:32]=[CH:31][C:30]4[C:25](=[CH:26][CH:27]=[CH:28][CH:29]=4)[N:24]=3)[CH:19]=2)[CH:9]=[C:10]([CH3:11])[C:5]=1[C:4]([O:3][CH2:1][CH3:2])=[O:14]

参加物

6

反応物 3

HCID 11430Potassium CarbonateHCID 75653Ethyl orsellinateHCID 145017072-(3-Chloromethylphenoxymethyl)quinoline hydrochloride

生成物 1

HCID 22241340Ethyl 2-hydroxy-6-methyl-4-[3-(quinolin-2-ylmethoxy)-benzyloxy]-benzoate

試薬・触媒・溶媒 2

HCID 67553Tetrabutylammonium Iodide触媒HCID 180Acetone溶媒

実験手順

2,4-Dihydroxy-6-methyl-benzoic acid ethyl ester (315 mg, 1.6 mmol) is combined with 2-(3-chloromethyl-phenoxymethyl)-quinoline hydrochloride (0.51 g, 1.6 mmol, example 49), tetrabutylammonium iodide (55 mg, 0.15 mmol) and potassium carbonate (0.48 g, 3.5 mmol) in acetone (9 mL). The reaction is heated at reflux 48 h. The reaction is partitioned between ethyl acetate and saturated ammonium chloride. The organic phase is washed with brine, dried over magnesium sulfate, filtered and concentrated to yield the crude product. This material is purified by column chromatography (silica, 3% ether in dichloromethane) to the title compound; m.p. 127–128° C., MS (ESI) 444 (M+H)+.

後処理

  1. temperatureThe reaction is heated
  2. temperatureat reflux 48 h
  3. customThe reaction is partitioned between ethyl acetate and saturated ammonium chloride
  4. washThe organic phase is washed with brine
  5. dry with materialdried over magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated

出典と根拠

ORDレコード
ord-80967c531b3b4f73860cc670aab8d41e
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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