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

HRID 892188Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 892188
[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]

Komponenten

6

Edukt 3

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

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 67553Tetrabutylammonium IodideKatalysatorHCID 180AcetoneLösungsmittel

Versuchsvorschrift

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)+.

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-80967c531b3b4f73860cc670aab8d41e
Quelldatensatz
uspto-grants-2006_02
Patentnummer
US07005440B1

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