Ammonium Chloride → 5-Acetoxy-4,6-di-tert-butyl-2-(1-octenyl)benzofuran

HRID 1452381

Reaktionsgleichung

Reaktionsgleichung von HRID 1452381
C([Li])CCC.[Br-].[CH2:7]([P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH3:13].[C:33]([O:36][C:37]1[C:38]([C:52]([CH3:55])([CH3:54])[CH3:53])=[CH:39][C:40]2[O:44][C:43]([CH:45]=O)=[CH:42][C:41]=2[C:47]=1[C:48]([CH3:51])([CH3:50])[CH3:49])(=[O:35])[CH3:34].[Cl-].[NH4+]>O1CCCC1.CCCCC>[C:33]([O:36][C:37]1[C:38]([C:52]([CH3:54])([CH3:53])[CH3:55])=[CH:39][C:40]2[O:44][C:43]([CH:45]=[CH:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH3:13])=[CH:42][C:41]=2[C:47]=1[C:48]([CH3:49])([CH3:50])[CH3:51])(=[O:35])[CH3:34]

Komponenten

7

Edukt 4

HCID 25517Ammonium ChlorideHCID 2724567Heptyltriphenylphosphonium bromideHCID 229186695-Acetoxy-4,6-di-tert-butyl-2-formylbenzofuranHCID 178418339Butyllithium

Produkt 1

HCID 537687215-Acetoxy-4,6-di-tert-butyl-2-(1-octenyl)benzofuranAusbeute 97 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 8003PentaneLösungsmittelHCID 8028TetrahydrofuranLösungsmittel2×

Versuchsvorschrift

A pentane solution (6.0 ml) of 1.6M n-butyllithium was added dropwise to a solution of n-heptyltriphenylphosphonium bromide (4.2 g) in tetrahydrofuran (30 ml) under a nitrogen atmosphere. After stirring the mixture at room temperature for 90 min, a solution of 5-acetoxy-4,6-di-tert-butyl-2-formylbenzofuran (2.54 g) in tetrahydrofuran (20 ml) was added dropwise. Subsequently, the mixture was heated under reflux for 1 h and, after cooling, a saturated aqueous solution of ammonium chloride was added and the mixture was subjected to extraction with ethyl acetate. The organic layer was washed with water and saturated brine, dried over anhydrous magnesium sulfate and concentrated. The concentrate was purified by silica gel chromatography (10% ethyl acetate in n-hexane) to afford 5-acetoxy-4,6-di-tert-butyl-2-(1-octenyl)benzofuran [3.1 g (yield, 97%)] as a colorless oil.

Aufarbeitung

  1. temperatureSubsequently, the mixture was heated
  2. temperatureunder reflux for 1 h
  3. temperatureafter cooling
  4. extractionthe mixture was subjected to extraction with ethyl acetate
  5. washThe organic layer was washed with water and saturated brine
  6. dry with materialdried over anhydrous magnesium sulfate
  7. concentrationconcentrated
  8. customThe concentrate was purified by silica gel chromatography (10% ethyl acetate in n-hexane)

Quellen und Nachweise

ORD-Eintrag
ord-2ab65c6669334c7c813729a38036c741
Quelldatensatz
uspto-grants-1997_02
Patentnummer
US05606089

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