Dimethylformamide → Ethyl 4-[2-(1,2,3,4-Tetramethoxy-6,7,8,9-tetrahydro-5H-benzo[a]cyclohepten-7-yl)ethoxy]benzoate

HRID 2268495Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2268495
I[CH2:2][CH2:3][CH:4]1[CH2:10][CH2:9][C:8]2[C:11]([O:21][CH3:22])=[C:12]([O:19][CH3:20])[C:13]([O:17][CH3:18])=[C:14]([O:15][CH3:16])[C:7]=2[CH2:6][CH2:5]1.[OH:23][C:24]1[CH:32]=[CH:31][C:27]([C:28]([O-])=[O:29])=[CH:26][CH:25]=1.[C:33](=O)([O-])[O-].[K+].[K+].CN([CH:42]=[O:43])C>O>[CH3:16][O:15][C:14]1[C:7]2[CH2:6][CH2:5][CH:4]([CH2:3][CH2:2][O:23][C:24]3[CH:32]=[CH:31][C:27]([C:28]([O:43][CH2:42][CH3:33])=[O:29])=[CH:26][CH:25]=3)[CH2:10][CH2:9][C:8]=2[C:11]([O:21][CH3:22])=[C:12]([O:19][CH3:20])[C:13]=1[O:17][CH3:18]

Komponenten

6

Edukt 4

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 183485187-(2-Iodoethyl)-1,2,3,4-tetramethoxy-6,7,8,9-tetrahydro-5H-benzo[a]cyclohepteneHCID 178524487HCID 178524487, Verbindung

Produkt 1

HCID 18348644Ethyl 4-[2-(1,2,3,4-Tetramethoxy-6,7,8,9-tetrahydro-5H-benzo[a]cyclohepten-7-yl)ethoxy]benzoate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Versuchsvorschrift

The mixture of 7-(2-iodoethyl)-1,2,3,4-tetramethoxy-6,7,8,9-tetrahydro-5H-benzo[a]cycloheptene (1.00 g), 4-hydroxybenzoate (593 mg), potassium carbonate (987 mg), and DMF (10 ml) was stirred at room temperature for 12 hr. The reaction mixture was diluted with water and extracted with ethyl acetate. The organic layer was washed with water and saturated aqueous sodium chloride, and dried. The solvent was removed in vacuo. The residue was purified by alumina column chromatography (hexane to hexane:ethyl acetate=15:1) and then with recrystallization from hexane-ethyl acetate to yield the entitled compound (910 mg) as crystals.

Aufarbeitung

  1. extractionextracted with ethyl acetate
  2. washThe organic layer was washed with water and saturated aqueous sodium chloride
  3. customdried
  4. customThe solvent was removed in vacuo
  5. customThe residue was purified by alumina column chromatography (hexane to hexane:ethyl acetate=15:1)
  6. customwith recrystallization from hexane-ethyl acetate

Quellen und Nachweise

ORD-Eintrag
ord-4d4276f4cfb847e8a1a206fcd8a0ed35
Quelldatensatz
uspto-grants-2001_12
Patentnummer
US06326369B1

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