Reaktion #957031

Reaktionsgleichung

1-[4-(2,2-diethoxy-ethoxy)-phenyl]-cyclopropanecarboxylic acid

→

1-(benzofuran-5-yl)cyclopropanecarboxylic acid

Ausbeute 11.4%

Lösungsmittel

xylene

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.ADDITIONwas added PPA (22.2 g, 64.9 mmol) at room temperature
2. 2
   TemperaturThe mixture was heated
3. 3
   Temperaturwas cooled to room temperature
4. 4
   Sonstigedecanted from the PPA
5. 5
   SonstigeThe solvent was evaporated under vacuum
6. 6
   Sonstigeto obtain the crude product, which
7. 7
   Sonstigewas purified by preparative HPLC

Vorschrift

To a suspension of crude 1-[4-(2,2-diethoxy-ethoxy)-phenyl]-cyclopropanecarboxylic acid (20 g, ˜65 mmol) in xylene (100 mL) was added PPA (22.2 g, 64.9 mmol) at room temperature. The mixture was heated at reflux (140° C.) for 1 hour before it was cooled to room temperature and decanted from the PPA. The solvent was evaporated under vacuum to obtain the crude product, which was purified by preparative HPLC to provide 1-(benzofuran-5-yl)cyclopropanecarboxylic acid (1.5 g, 5%). 1H NMR (400 MHz, DMSO-d6) δ 12.25 (br s, 1H), 7.95 (d, J=2.8 Hz, 1H), 7.56 (d, J=2.0 Hz, 1H), 7.47 (d, J=11.6 Hz, 1H), 7.25 (dd, J=2.4, 11.2 Hz, 1H), 6.89 (d, J=1.6 Hz, 1H), 1.47-1.44 (m, 2H), 1.17-1.14 (m, 2H).

Quelle