Reaktion #501828

Reaktionsgleichung

3,4-epoxy-3-(4'-fluorophenyl)-1-butyne

H2O

→

2-(4'-fluorophenyl)furan

Ausbeute 58.0%

Lösungsmittel

H2SO4

ethanol

Reaktionsbedingungen

Aufarbeitung

1. 1
   TemperaturThe reaction mixture was refluxed for 0.25 hour
2. 2
   Extraktionthe aqueous phase was extracted twice with hexanes
3. 3
   Trocknendried (MgSO4)
4. 4
   Einengenconcentrated under reduced pressure

Vorschrift

To a solution of 0.7 g HgSO4 in 40 mL of 2N H2SO4 was added 5.0 g (31 mmol) of the 3,4-epoxy-3-(4'-fluorophenyl)-1-butyne in 40 mL of absolute ethanol, dropwise. The reaction mixture was refluxed for 0.25 hour and cooled to 23° C. After addition to 50 mL of H2O, the aqueous phase was extracted twice with hexanes. The hexane layers were combined, dried (MgSO4) and concentrated under reduced pressure. Sublimation (90° C. at 0.2 mmHg) of the residue yielded 2.9 g (58%) of the 2-(4'-fluorophenyl)furan as a solid (m.p. 84°-86° C.) homogeneous by spectroscopic criteria; IR (film) 1571, 1505, 1223, 1152, 785 cm-1 ; 1HNMR (80 MHz, CDCl3) 7.5-7.0 (m, 6H), 6.65 (m, 1H).

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