Tetrahydrofuran → Ethyl 10-(6-bromo-2,3,4,5-tetramethoxyphenyl)-9,9-diethoxycarbonyldecanoate

HRID 2268441Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2268441
C1COCC1.[CH2:6]([O:8][C:9]([CH:11]([CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][C:24]([O:26][CH2:27][CH3:28])=[O:25])[C:12]([O:14][CH2:15][CH3:16])=[O:13])=[O:10])[CH3:7].[H-].[Na+].[Br:31][C:32]1[C:37]([CH2:38]Br)=[C:36]([O:40][CH3:41])[C:35]([O:42][CH3:43])=[C:34]([O:44][CH3:45])[C:33]=1[O:46][CH3:47]>[Cl-].[NH4+]>[Br:31][C:32]1[C:37]([CH2:38][C:11]([C:9]([O:8][CH2:6][CH3:7])=[O:10])([C:12]([O:14][CH2:15][CH3:16])=[O:13])[CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][C:24]([O:26][CH2:27][CH3:28])=[O:25])=[C:36]([O:40][CH3:41])[C:35]([O:42][CH3:43])=[C:34]([O:44][CH3:45])[C:33]=1[O:46][CH3:47]

Komponenten

6

Edukt 4

HCID 8028Tetrahydrofuran3×HCID 24758Sodium hydrideHCID 183486201-Bromo-6-bromomethyl-2,3,4,5-tetramethoxybenzeneHCID 18348648Ethyl 2,9-diethoxycarbonylnonanoate

Produkt 1

HCID 18348563Ethyl 10-(6-bromo-2,3,4,5-tetramethoxyphenyl)-9,9-diethoxycarbonyldecanoateAusbeute 65,6 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 25517Ammonium ChlorideLösungsmittel

Versuchsvorschrift

A THF (10 ml) solution of ethyl 2,9-diethoxycarbonylnonanoate (8.86 g, 26.8 mmols) was dropwise added to a THF (90 ml) suspension of sodium hydride (60% oily, 1.29 g, 32.2 mmols) at room temperature. The reaction mixture was stirred for 2 hours, and then a THF (10 ml) solution of 1-bromo-6-bromomethyl-2,3,4,5-tetramethoxybenzene (10.9 g, 29.5 mmols) was dropwise added at room temperature, and stirring was continued for additional 2 hours. The reaction mixture was diluted with a saturated aqueous ammonium chloride solution and then concentrated in vacuo. The residue was extracted with ethyl acetate, and the resulting organic layer was washed with water and a saturated aqueous sodium chloride solution, then dried, and concentrated in vacuo. The crude product thus obtained was purified by silica gel column chromatography (hexane:ethyl acetate=10:1 to 4:1) to obtain the entitled compound (10.9 g) as an oil.

Aufarbeitung

  1. stirringstirring
  2. waitwas continued for additional 2 hours
  3. concentrationconcentrated in vacuo
  4. extractionThe residue was extracted with ethyl acetate
  5. washthe resulting organic layer was washed with water
  6. dry with materiala saturated aqueous sodium chloride solution, then dried
  7. concentrationconcentrated in vacuo
  8. customThe crude product thus obtained
  9. customwas purified by silica gel column chromatography (hexane:ethyl acetate=10:1 to 4:1)

Quellen und Nachweise

ORD-Eintrag
ord-c4c97b25ee6b480188671156d1539fe8
Quelldatensatz
uspto-grants-2001_12
Patentnummer
US06326369B1

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