Hydrochloric Acid → 2-(4-Benzyloxy-2,6-dichloro-benzyl)-2-(2,2-dimethoxy-ethyl)-malonic acid diethyl ester

HRID 1161767Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1161767
[CH2:1]([O:3][C:4](=[O:17])[CH:5]([CH2:11][CH:12]([O:15][CH3:16])[O:13][CH3:14])[C:6]([O:8][CH2:9][CH3:10])=[O:7])[CH3:2].[CH2:18]([O:25][C:26]1[CH:27]=[C:28]([Cl:35])[C:29]([CH2:33]Br)=[C:30]([Cl:32])[CH:31]=1)[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.Cl>C1COCC1>[CH2:9]([O:8][C:6](=[O:7])[C:5]([CH2:33][C:29]1[C:28]([Cl:35])=[CH:27][C:26]([O:25][CH2:18][C:19]2[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=2)=[CH:31][C:30]=1[Cl:32])([CH2:11][CH:12]([O:13][CH3:14])[O:15][CH3:16])[C:4]([O:3][CH2:1][CH3:2])=[O:17])[CH3:10]

Komponenten

5

Edukt 3

HCID 313Hydrochloric AcidHCID 14215238Diethyl (2,2-dimethoxyethyl)malonateHCID 592994282-Bromomethyl-1,3-dichloro-5-benzyloxy-benzene

Produkt 1

HCID 686483152-(4-Benzyloxy-2,6-dichloro-benzyl)-2-(2,2-dimethoxy-ethyl)-malonic acid diethyl esterAusbeute 83,6 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel2×

Versuchsvorschrift

Cool 2-(2,2-Dimethoxy-ethyl)-malonic acid diethyl ester (4.5 g, 16.3 mmol) in 50 mL THF to −78° C. and add lithium hexamethylsilane amide (1M, 17 mL) drop wise. After 15 min, add 5-benzyloxy-2-bromomethyl-1,3-dichloro-benzene (17.9 mmol 6.2 g) in 10 mL THF. Warm this mixture to ambient temperature, acidify with 1N HCl, and extract with ethyl acetate. Concentrate the organics and purify by normal phase column chromatography to afford the title compound as a white solid (7.0 g, 80%).

Aufarbeitung

  1. extractionextract with ethyl acetate
  2. concentrationConcentrate the organics and
  3. custompurify by normal phase column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-a666d68e49bb4753a72a92f0d2d38f37
Quelldatensatz
uspto-grants-2010_10
Patentnummer
US07820659B2

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