Tetrahydrofuran → 4-n-Butylidene-4,5,6,7-tetrahydrobenzo[b]furan

HRID 650595

Reaktionsgleichung

Reaktionsgleichung von HRID 650595
O=[C:2]1[C:10]2[CH:9]=[CH:8][O:7][C:6]=2[CH2:5][CH2:4][CH2:3]1.[CH2:11]1[CH2:15]O[CH2:13][CH2:12]1.C([Mg]Br)CCC.[NH4+].[Cl-]>CCOC(C)=O>[CH:15](=[C:2]1[C:10]2[CH:9]=[CH:8][O:7][C:6]=2[CH2:5][CH2:4][CH2:3]1)[CH2:11][CH2:12][CH3:13]

Komponenten

6

Edukt 4

HCID 8028TetrahydrofuranHCID 25517Ammonium ChlorideHCID 27335414,5,6,7-Tetrahydro-1-benzofuran-4-oneHCID 178418682HCID 178418682, Verbindung

Produkt 1

HCID 545187564-n-Butylidene-4,5,6,7-tetrahydrobenzo[b]furan

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

To a mixture of 4-oxo-4,5,6,7-tetrahydrobenzo[b]furan (20.06 g) and THF (200 ml) was added dropwise 2M n-butylmagnesium bromide with ice-water cooling over 15 minutes. The mixture was stirred at r.t. overnight. The reaction mixture was poured into a mixture of a saturated aqueous solution of NH4Cl and AcOEt. The separated organic layer was washed with water and brine, and dried over MgSO4, and evaporated. The resulting oil was purified by chromatography on SiO2 (CHCl3 as eluent) to give 4-n-butylidene-4,5,6,7-tetrahydrobenzo[b]furan as a yellow oil (12.06 g).

Aufarbeitung

  1. washThe separated organic layer was washed with water and brine
  2. dry with materialdried over MgSO4
  3. customevaporated
  4. customThe resulting oil was purified by chromatography on SiO2 (CHCl3 as eluent)

Quellen und Nachweise

ORD-Eintrag
ord-274df34808e2475186d75710ee35a1fe
Quelldatensatz
uspto-grants-2001_08
Patentnummer
US06274619B1

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