Sodium hydride → 6-(6-(benzyloxy)benzofuran-2-yl)-3,5-dimethyl-4-hydroxy-2H-pyran-2-one

HRID 1357207

Reaktionsgleichung

Reaktionsgleichung von HRID 1357207
[CH3:1][CH:2]([C:7](=[O:10])[CH2:8][CH3:9])[C:3]([O:5][CH3:6])=[O:4].[H-].[Na+].[Li]CCCC.[CH2:18]([O:25][C:26]1[CH:38]=[CH:37][C:29]2[CH:30]=[C:31](C(OC)=O)[O:32][C:28]=2[CH:27]=1)[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.[Cl-].[NH4+]>C1COCC1>[CH2:18]([O:25][C:26]1[CH:38]=[CH:37][C:29]2[CH:30]=[C:31]([C:6]3[O:5][C:3](=[O:4])[C:2]([CH3:1])=[C:7]([OH:10])[C:8]=3[CH3:9])[O:32][C:28]=2[CH:27]=1)[C:19]1[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=1

Komponenten

7

Edukt 5

HCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 545860Methyl 2-methyl-3-oxopentanoateHCID 12082973Methyl 6-(phenylmethoxy)-2-benzofurancarboxylateHCID 178418339Butyllithium

Produkt 1

HCID 547294826-(6-(benzyloxy)benzofuran-2-yl)-3,5-dimethyl-4-hydroxy-2H-pyran-2-one

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel3×

Reaktionsbedingungen

Temperatur
-78 °C

Versuchsvorschrift

A solution of methyl 2-methyl-3-oxopentanoate (3.24 g) in THF (30 ml) was slowly added to a suspension of NaH (900 mg) in THF (50 ml) at 0° C., and after stirring for 10 minutes, the mixture was cooled to −78° C. and 1.58 M n-BuLi (14.2 ml) was slowly added dropwise. After stirring the reaction solution at −78° C. for 30 minutes, a solution of methyl 6-(benzyloxy)benzofuran-2-carboxylate (4.26 g) in THF (15 ml) was slowly added and the mixture was stirred at −78° C. for 4 hours. A saturated ammonium chloride aqueous solution was added to the reaction solution, and after bringing it to room temperature, extraction was performed with AcOEt and the organic layer was dried with MgSO4 and then filtered and concentrated. The residue was dissolved in MeOH (30 ml) and THF (10 ml), a 4 N lithium hydroxide aqueous solution (5 ml) and water (50 ml) were added, and after stirring at room temperature for 4 hours, a saturated KHSO4 aqueous solution (30 ml) was slowly added. The deposited yellow precipitate was filtered off and rinsed with AcOEt to obtain 6-(6-(benzyloxy)benzofuran-2-yl)-3,5-dimethyl-4-hydroxy-2H-pyran-2-one.

Aufarbeitung

  1. stirringAfter stirring the reaction solution at −78° C. for 30 minutes
  2. stirringthe mixture was stirred at −78° C. for 4 hours
  3. customto room temperature
  4. extractionextraction
  5. dry with materialthe organic layer was dried with MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. dissolutionThe residue was dissolved in MeOH (30 ml)
  9. additionTHF (10 ml), a 4 N lithium hydroxide aqueous solution (5 ml) and water (50 ml) were added
  10. stirringafter stirring at room temperature for 4 hours
  11. additiona saturated KHSO4 aqueous solution (30 ml) was slowly added
  12. filtrationThe deposited yellow precipitate was filtered off
  13. washrinsed with AcOEt

Quellen und Nachweise

ORD-Eintrag
ord-4a7816112a104fd0a1be265bccd43124
Quelldatensatz
uspto-grants-2003_07
Patentnummer
US06589984B1

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