Ethyl Acetate → HCID 58047427, Verbindung

HRID 1888714Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1888714
O[CH:2]([C:4]1[O:5][C:6]2[CH:12]=[C:11]([C:13]([O:15][CH3:16])=[O:14])[CH:10]=[CH:9][C:7]=2[CH:8]=1)[CH3:3].P([N:33]=[N+:34]=[N-:35])(OC1C=CC=CC=1)(OC1C=CC=CC=1)=O.C1CCN2C(=NCCC2)CC1.C(OCC)(=O)C>C1(C)C=CC=CC=1>[N:33]([CH:2]([C:4]1[O:5][C:6]2[CH:12]=[C:11]([C:13]([O:15][CH3:16])=[O:14])[CH:10]=[CH:9][C:7]=2[CH:8]=1)[CH3:3])=[N+:34]=[N-:35]

Komponenten

6

Edukt 4

HCID 8857Ethyl AcetateHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 123414Diphenylphosphoryl azideHCID 22481692HCID 22481692, Verbindung

Produkt 1

HCID 58047427HCID 58047427, VerbindungAusbeute 99,7 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1140TolueneLösungsmittel

Versuchsvorschrift

To a solution of methyl 2-(1-hydroxyethyl)-1-benzofuran-6-carboxylate (1.10 g, 4.99 mmol) in toluene (20 mL) were added diphenyl azidophosphate (1.62 mL, 7.50 mmol) and DBU (1.50 mL, 9.98 mmol), and the mixture was stirred at room temperature for 2.5 hr. Ethyl acetate was added thereto, and the mixture was washed with water, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure, and the obtained residue was purified by silica gel column chromatography (hexane:ethyl acetate=20:1 to 2:3) to give the title compound (1.22 g, yield 88%) as an oil.

Aufarbeitung

  1. washthe mixture was washed with water
  2. dry with materialdried over anhydrous magnesium sulfate
  3. customThe solvent was evaporated under reduced pressure
  4. customthe obtained residue was purified by silica gel column chromatography (hexane:ethyl acetate=20:1 to 2:3)

Quellen und Nachweise

ORD-Eintrag
ord-6c988b22b153412db8cb5047933afeae
Quelldatensatz
uspto-grants-2013_08
Patentnummer
US08501804B2

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