Ammonium Chloride → (4-Bromonaphthalen-2-yl)-(5-methoxybenzo-[b]thiophen-2-yl)methanol

HRID 550245Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 550245
CCCCCC.C([Li])CCC.[CH3:12][O:13][C:14]1[CH:22]=[CH:21][C:17]2[S:18][CH:19]=[CH:20][C:16]=2[CH:15]=1.[Br:23][C:24]1[C:33]2[C:28](=[CH:29][CH:30]=[CH:31][CH:32]=2)[CH:27]=[C:26]([CH:34]=[O:35])[CH:25]=1.[Cl-].[NH4+]>C1COCC1>[Br:23][C:24]1[C:33]2[C:28](=[CH:29][CH:30]=[CH:31][CH:32]=2)[CH:27]=[C:26]([CH:34]([C:19]2[S:18][C:17]3[CH:21]=[CH:22][C:14]([O:13][CH3:12])=[CH:15][C:16]=3[CH:20]=2)[OH:35])[CH:25]=1

Komponenten

6

Edukt 4

HCID 25517Ammonium ChlorideHCID 36324255-Methoxy-1-benzothiopheneHCID 543381284-Bromonaphthalene-2-carbaldehydeHCID 178418244HCID 178418244, Verbindung

Produkt 1

HCID 67157589(4-Bromonaphthalen-2-yl)-(5-methoxybenzo-[b]thiophen-2-yl)methanolAusbeute 80,7 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel2×

Versuchsvorschrift

In a nitrogen stream, an n-butyllithium hexane solution (1.6 M, 1.48 ml, 2.36 mmol) was added dropwise to a solution of 5-methoxybenzo[b]thiophene (388 mg, 2.36 mmol) in THF (6 ml) at −78° C. and the reaction solution was stirred at the same temperature for 10 minutes. To this solution, a solution of 4-bromonaphthalene-2-carbaldehyde (530 mg, 2.25 mmol) in THF (4 ml) was added dropwise. The reaction mixture was stirred at the same temperature for two hours, and then a saturated ammonium chloride aqueous solution added and the mixture was extracted with ethyl acetate. The organic layer was washed with a saturated sodium chloride aqueous solution and dried (anhydrous magnesium sulfate), and then the solvent was distilled under reduced pressure. The obtained residue was purified by silica gel column chromatography [developing solution=ethyl acetate:n-hexane (1:10)] to obtain the title compound (725 mg, 77%).

Aufarbeitung

  1. stirringThe reaction mixture was stirred at the same temperature for two hours
  2. extractionthe mixture was extracted with ethyl acetate
  3. washThe organic layer was washed with a saturated sodium chloride aqueous solution
  4. dry with materialdried (anhydrous magnesium sulfate)
  5. distillationthe solvent was distilled under reduced pressure
  6. customThe obtained residue was purified by silica gel column chromatography [developing solution=ethyl acetate:n-hexane (1:10)]

Quellen und Nachweise

ORD-Eintrag
ord-dfa510d4843b41ecb6227898c344d178
Quelldatensatz
uspto-grants-2011_05
Patentnummer
US07943748B2

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