Hydrochloric Acid → ethyl 8-chloro-4-hydroxy-2-oxo-2',3',5',6'-tetrahydro-4H-spiro[naphthalene-1,4'-pyran]-3-carboxylate

HRID 1868940Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1868940
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4](/[C:8](/[OH:15])=[CH:9]/[C:10]([O:12][CH2:13][CH3:14])=[O:11])[C:3]=1[C:16]1([C:22](OCC)=[O:23])[CH2:21][CH2:20][O:19][CH2:18][CH2:17]1.CC[O-].[Na+].Cl>CCO.CCOC(C)=O>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]2[C:3]=1[C:16]1([CH2:17][CH2:18][O:19][CH2:20][CH2:21]1)[C:22](=[O:23])[CH:9]([C:10]([O:12][CH2:13][CH3:14])=[O:11])[CH:8]2[OH:15]

Komponenten

6

Edukt 3

HCID 313Hydrochloric AcidHCID 2723922Sodium ethoxideHCID 86629261(Z)-ethyl 4-(2-chloro-6-(3-ethoxy-1-hydroxy-3-oxoprop-1-enyl)phenyl)-tetrahydro-2H-pyran-4-carboxylate

Produkt 1

HCID 67099930ethyl 8-chloro-4-hydroxy-2-oxo-2',3',5',6'-tetrahydro-4H-spiro[naphthalene-1,4'-pyran]-3-carboxylateAusbeute 80,5 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 702EthanolLösungsmittel2×HCID 8857Ethyl AcetateLösungsmittel

Reaktionsbedingungen

Temperatur
60 °C

Versuchsvorschrift

A mixture of (Z)-ethyl 4-(2-chloro-6-(3-ethoxy-1-hydroxy-3-oxoprop-1-enyl)phenyl)-tetrahydro-2H-pyran-4-carboxylate (0.38 g, 0.99 mmol) in 5 mL EtOH was treated with NaOEt (freshly made from 0.1 g Na and 5 mL EtOH), and stirred at 60° C. for 2 hours. The mixture was cooled to room temperature and diluted with 100 mL EtOAc, neutralized with 5N HCl to pH 5, washed with water (20 mL), saturated NaCl (20 mL), dried over anhydrous sodium sulfate and concentrated. The concentrate was purified by column chromatography (10-40% EtOAc/hexane) to give 0.27 g yellow solid. MS m/e: (M+H)+ 337.

Aufarbeitung

  1. temperatureThe mixture was cooled to room temperature
  2. washwashed with water (20 mL), saturated NaCl (20 mL)
  3. dry with materialdried over anhydrous sodium sulfate
  4. concentrationconcentrated
  5. customThe concentrate was purified by column chromatography (10-40% EtOAc/hexane)

Quellen und Nachweise

ORD-Eintrag
ord-05d9249ad98a4b828a33d99ec5771dec
Quelldatensatz
uspto-grants-2009_12
Patentnummer
US07635715B2

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