Ethyl Bromide → Diethyl 1-(ethyloxy)-4-hydroxy-2,3-naphthalenedicarboxylate

HRID 913171Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 913171
Br[CH2:2][CH3:3].[OH:4][C:5]1[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[C:8]([OH:15])=[C:7]([C:16]([O:18][CH2:19][CH3:20])=[O:17])[C:6]=1[C:21]([O:23][CH2:24][CH3:25])=[O:22].C(=O)([O-])[O-].[K+].[K+]>CC(C)=O>[CH2:2]([O:4][C:5]1[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[C:8]([OH:15])=[C:7]([C:16]([O:18][CH2:19][CH3:20])=[O:17])[C:6]=1[C:21]([O:23][CH2:24][CH3:25])=[O:22])[CH3:3]

Komponenten

5

Edukt 3

HCID 6332Ethyl BromideHCID 11430Potassium CarbonateHCID 431092,3-Diethyl 1,4-dihydroxy-2,3-naphthalenedicarboxylate

Produkt 1

HCID 58012479Diethyl 1-(ethyloxy)-4-hydroxy-2,3-naphthalenedicarboxylateAusbeute 60,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 180AcetoneLösungsmittel

Versuchsvorschrift

Bromoethane (0.359 g, 3.29 mmol) was added to a stirred solution of diethyl 1,4-dihydroxy-2,3-naphthalenedicarboxylate (1 g, 3.29 mmol) and potassium carbonate (0.454 g, 3.29 mmol) in acetone (25 ml). The reaction mixture was refluxed for 24 hours under an atmosphere of argon. The resulting mixture was evaporated and the residue was partitioned between 2× ethylacetate and water. The combined organics were washed with water and dried over magnesium sulphate. The orange oil was purified by chromatography on silica gel, eluting with ethyl acetate (0-10%) in hexane to give the title compound as a clear oil (0.661 g, 1.99 mmol). LC/MS: Rt=3.63, [MH]− 331.

Aufarbeitung

  1. temperatureThe reaction mixture was refluxed for 24 hours under an atmosphere of argon
  2. customThe resulting mixture was evaporated
  3. customthe residue was partitioned between 2× ethylacetate and water
  4. washThe combined organics were washed with water
  5. dry with materialdried over magnesium sulphate
  6. customThe orange oil was purified by chromatography on silica gel
  7. washeluting with ethyl acetate (0-10%) in hexane

Quellen und Nachweise

ORD-Eintrag
ord-0a674e5155784048ad31f92153c5cde8
Quelldatensatz
uspto-grants-2011_09
Patentnummer
US08026270B2

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