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

HRID 892188노트

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HRID 892188 반응식
[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]

참가 물질

6

반응물 3

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

생성물 1

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

시약·촉매·용매 2

HCID 67553Tetrabutylammonium Iodide촉매HCID 180Acetone용매

실험 절차

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)+.

후처리

  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

출처 및 근거

ORD 기록
ord-80967c531b3b4f73860cc670aab8d41e
출처 데이터셋
uspto-grants-2006_02
특허 번호
US07005440B1

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