Butyl iodide → 2-butyl-6-methoxy-3,4-dihydro-1(2H)-naphthalenone

HRID 2113676

Reaktionsgleichung

Reaktionsgleichung von HRID 2113676
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[C:9](=[O:13])[CH2:8][CH2:7][CH2:6]2.I[CH2:15][CH2:16][CH2:17][CH3:18].[H-].[Na+]>O1CCCC1>[CH2:15]([CH:8]1[CH2:7][CH2:6][C:5]2[C:10](=[CH:11][CH:12]=[C:3]([O:2][CH3:1])[CH:4]=2)[C:9]1=[O:13])[CH2:16][CH2:17][CH3:18]

Komponenten

5

Edukt 3

HCID 10962Butyl iodideHCID 141126-Methoxy-alpha-tetraloneHCID 24758Sodium hydride

Produkt 1

HCID 586040732-butyl-6-methoxy-3,4-dihydro-1(2H)-naphthalenone

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

A mixture of 6-methoxy-3,4-dihydro-1(2H)-naphthalenone (400 mg, 2.27 mmol), iodobutane (0.284 mL, 2.5 mmol), NaH (98 mg of a 61.1% dispersion in mineral oil, 2.5 mmol), and anhydrous tetrahydrofuran (THF, 1 mL) was placed under a N2 atmosphere and stirred at room temperature for 15.5 hours. The mixture was partitioned between EtOAc (20 mL) and water (30 mL) containing 2N HCl (3 mL). The organic phase was washed with brine (20 mL), dried over MgSO4, filtered, and evaporated under vacuum to afford an oil. The crude product was purified by preparative layer chromatography on five 0.1×20×20 cm silica gel GF plates (Analtech, Newark, Del.), developing with CH2Cl2. The UV visible product band was eluted with EtOAc and the eluant evaporated under vacuum to provide 2-butyl-6-methoxy-3,4-dihydro-1(2H)-naphthalenone as a clear oil.

Aufarbeitung

  1. customThe mixture was partitioned between EtOAc (20 mL) and water (30 mL)
  2. additioncontaining 2N HCl (3 mL)
  3. washThe organic phase was washed with brine (20 mL)
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. customevaporated under vacuum
  7. customto afford an oil
  8. customThe crude product was purified by preparative layer chromatography on five 0.1×20×20 cm silica gel GF plates (Analtech, Newark, Del.)
  9. washThe UV visible product band was eluted with EtOAc
  10. customthe eluant evaporated under vacuum

Quellen und Nachweise

ORD-Eintrag
ord-7d06554a428c4e888c8f720f297954f1
Quelldatensatz
uspto-grants-2008_10
Patentnummer
US07432284B2

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