Hexane → 5,6,7-Trimethoxy-2-vinylnaphthalene

HRID 1267651Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1267651
[CH3:1]CCCCC.C([Li])(C)(C)C.[CH3:12][O:13][C:14]1[C:23]([O:24][CH3:25])=[C:22]([O:26][CH3:27])[CH:21]=[C:20]2[C:15]=1[CH:16]=[CH:17][C:18]([CH:28]=O)=[CH:19]2>[Br-].C[P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.C1COCC1>[CH3:12][O:13][C:14]1[C:23]([O:24][CH3:25])=[C:22]([O:26][CH3:27])[CH:21]=[C:20]2[C:15]=1[CH:16]=[CH:17][C:18]([CH:28]=[CH2:1])=[CH:19]2

Komponenten

6

Edukt 3

HCID 8058HexaneHCID 218916375,6,7-Trimethoxynaphthalene-2-carbaldehydeHCID 178418306HCID 178418306, Verbindung

Produkt 1

HCID 218915705,6,7-Trimethoxy-2-vinylnaphthalene

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 74505Methyltriphenyliphosphonium bromideKatalysatorHCID 8028TetrahydrofuranLösungsmittel2×

Versuchsvorschrift

Methyltriphenylphosphonium bromide (2.8 g) was suspended in dry THF (10 mL) under an argon atmosphere, and a hexane solution (3.3 mL) of 1.7 M tert-butyllithium was added to the suspension at −20° C. After the reaction mixture was warmed to room temperature and stirred for 1 hour, it was cooled again to −20° C., a solution of 5,6,7-trimethoxynaphthalene-2-carboaldehyde (1.26 g) in dry THF (30 mL) was added dropwise thereto, and the mixture was stirred overnight at room temperature. The solvent was distilled off, and water was added to the residue to conduct extraction with ethyl acetate. The resultant organic layer was washed with water and saturated brine, dried over anhydrous magnesium sulfate and then concentrated under reduced pressure. The residue was purified by column chromatography on silica gel (ethyl acetate:hexane=1:8) to obtain the title compound.

Aufarbeitung

  1. temperatureit was cooled again to −20° C.
  2. stirringthe mixture was stirred overnight at room temperature
  3. distillationThe solvent was distilled off
  4. additionwater was added to the residue
  5. extractionextraction with ethyl acetate
  6. washThe resultant organic layer was washed with water and saturated brine
  7. dry with materialdried over anhydrous magnesium sulfate
  8. concentrationconcentrated under reduced pressure
  9. customThe residue was purified by column chromatography on silica gel (ethyl acetate:hexane=1:8)

Quellen und Nachweise

ORD-Eintrag
ord-f838789849294b5abd478be0ce36fe77
Quelldatensatz
uspto-grants-2003_04
Patentnummer
US06552188B2

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