4-Methoxybenzyl alcohol → 2-Chloro-4-(4-methoxybenzyloxy)quinoline

HRID 430067Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 430067
[Cl:1][C:2]1[CH:11]=[C:10](Cl)[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[N:3]=1.[H-].[Na+].C1OCCOCCOCCOCCOC1.[CH3:30][O:31][C:32]1[CH:39]=[CH:38][C:35]([CH2:36][OH:37])=[CH:34][CH:33]=1>C1COCC1>[Cl:1][C:2]1[CH:11]=[C:10]([O:37][CH2:36][C:35]2[CH:38]=[CH:39][C:32]([O:31][CH3:30])=[CH:33][CH:34]=2)[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[N:3]=1

Komponenten

6

Edukt 4

HCID 77384-Methoxybenzyl alcoholHCID 24758Sodium hydrideHCID 3633615-Crown-5HCID 6075032,4-Dichloroquinoline

Produkt 1

HCID 183536712-Chloro-4-(4-methoxybenzyloxy)quinolineAusbeute 39 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

2,4-Dichloroquinoline (4.48 g, 25 mmol) was dissolved in dry THF (100 ml) and treated with sodium hydride (60% dispersion in oil, 5.62 g 25 mmol) under an argon atmosphere portion-wise over a period of 20 min. After a further 30 min the reaction mixture was treated with 15-crown-5 (5.62 g, 25 mmol) followed by 4-methoxybenzyl alcohol (3.44 g, 23 mmol). The reaction was stirred at room temperature overnight. The reaction mixture was then evaporated to low volume, and partitioned between water and ethyl acetate. The organic layer was washed with brine, dried (MgSO4) and evaporated. Chromatography on Kieselgel 60 eluting with 10% ethyl acetate in hexane afforded the title compound as a white solid (2.67 g, 39%); δH (CDCl3) 5.20 (2H, s), 6.83 (1H, s), 6.97 and 7.43 (4H, 2×d, J=8.6 Hz), 7.49 (1H, t, J=8.1 Hz), 7.70 (1H, t, J=8.2 Hz), 7.94 (1H, d, J=8.3 Hz), 8.17 (1H, d, J=8.2 Hz); MS (ES+) 300 (MH+, 10%). 121 (100).

Aufarbeitung

  1. customThe reaction mixture was then evaporated to low volume
  2. custompartitioned between water and ethyl acetate
  3. washThe organic layer was washed with brine
  4. dry with materialdried (MgSO4)
  5. customevaporated

Quellen und Nachweise

ORD-Eintrag
ord-361fc9a83b404743950446eea26116e0
Quelldatensatz
uspto-grants-2001_11
Patentnummer
US06320051B1

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