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

HRID 2289432

Reaktionsgleichung

Reaktionsgleichung von HRID 2289432
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-b734d03058194cb3b02b48b65a261790
Quelldatensatz
uspto-grants-2000_07
Patentnummer
US06093710

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