Hydrochloric Acid → 8-(cyclopentyloxy)-4-hydroxy-7-methoxy-2H-chromen-2-one

HRID 20626

Reaktionsgleichung

Reaktionsgleichung von HRID 20626
[CH:1]1([O:6][C:7]2[C:8]([OH:18])=[C:9]([C:15](=[O:17])[CH3:16])[CH:10]=[CH:11][C:12]=2[O:13][CH3:14])[CH2:5][CH2:4][CH2:3][CH2:2]1.[H-].[Na+].[C:21](=O)(OCC)[O:22]CC.Cl.CC(C)([O-])C.[K+]>O>[CH:1]1([O:6][C:7]2[C:12]([O:13][CH3:14])=[CH:11][CH:10]=[C:9]3[C:8]=2[O:18][C:21](=[O:22])[CH:16]=[C:15]3[OH:17])[CH2:2][CH2:3][CH2:4][CH2:5]1

Komponenten

7

Edukt 5

HCID 313Hydrochloric AcidHCID 7766Diethyl CarbonateHCID 24758Sodium hydrideHCID 23665647Potassium tert-butoxide2×HCID 687411251-[3-(cyclopentyloxy)-2-hydroxy-4-methoxyphenyl]Ethanone

Produkt 1

HCID 771747928-(cyclopentyloxy)-4-hydroxy-7-methoxy-2H-chromen-2-one

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Versuchsvorschrift

1-[3-(Cyclopentyloxy)-2-hydroxy-4-methoxyphenyl]ethanone (4.25 g, 17 mmol) was added portionwise to a mixture of sodium hydride (1.4 g, 60%, 35 mmol) and diethyl carbonate (30 mL) at rt under N2. The reaction was refluxed for 1 h and then cooled to rt. 10% Hydrochloric acid (30 mL) was added, and the mixture was stirred for 1 h. The reaction was diluted with water (100 mL) and extracted with ethyl acetate (200 mL×2). The combined extracts were dried, filtered, concentrated, and redissolved in t-butanol (50 mL). Potassium t-butoxide (4.0 g, 36 mmol) was added, and the reaction was refluxed. After 42 h, additional potassium t-butoxide (2.0 g, 18 mmol) was added. After an additional 2 d, the reaction was allowed to cool to rt, concentrated, diluted with 1N HCl (100 mL), and extracted with ethyl acetate (200 mL×2). The combined extracts were dried, filtered, concentrated, and purified by silica gel chromatography (3:2→0:1; hexanes:ethyl acetate) to give 8-(cyclopentyloxy)-4-hydroxy-7-methoxy-2H-chromen-2-one: MS (ESI): 277.1.

Aufarbeitung

  1. temperatureThe reaction was refluxed for 1 h
  2. extractionextracted with ethyl acetate (200 mL×2)
  3. customThe combined extracts were dried
  4. filtrationfiltered
  5. concentrationconcentrated
  6. dissolutionredissolved in t-butanol (50 mL)
  7. temperaturethe reaction was refluxed
  8. waitAfter 42 h
  9. waitAfter an additional 2 d
  10. temperatureto cool to rt
  11. concentrationconcentrated
  12. additiondiluted with 1N HCl (100 mL)
  13. extractionextracted with ethyl acetate (200 mL×2)
  14. customThe combined extracts were dried
  15. filtrationfiltered
  16. concentrationconcentrated
  17. custompurified by silica gel chromatography (3:2→0:1; hexanes:ethyl acetate)

Quellen und Nachweise

ORD-Eintrag
ord-bc842910be95438d975c07ba9056f9d3
Quelldatensatz
uspto-grants-2010_06
Patentnummer
US07745646B2

Verknüpfte Notizen

Wird geladen…