Reaktion #163418

Reaktionsgleichung

1-(3′,4′-Dichloro-2-fluorobiphenyl-4-yl)cyclopropanecarboxylic acid

dicyclohexylcarbodiimide

oxiran-2-ylmethanol

→

1-(3′,4′-dichloro-2-fluorobiphenyl-4-yl)cyclopropane carboxylic acid oxiranylmethyl ester

Ausbeute 42.7%

Lösungsmittel

DCM

Reaktionsbedingungen

Aufarbeitung

1. 1
   Filtrationit was filtered
2. 2
   Sonstigethe filtrate was evaporated to dryness
3. 3
   Sonstigeto afford 4.4 g of crude
4. 4
   SonstigeThe crude was purified by gradient flash chromatography
5. 5
   Wascheneluting with petroleum ether/EtOAc (from 97/3 to 90/10 v/v)

Vorschrift

1-(3′,4′-Dichloro-2-fluorobiphenyl-4-yl)cyclopropanecarboxylic acid (2.00 g, 6.15 mmol), dicyclohexylcarbodiimide (DCC, 2.54 g, 12.30 mmol), 4-dimethyl-aminopyridine (DMAP, 0.075 g, 0.614 mmol), and oxiran-2-ylmethanol (0.490 ml, 7.38 mmol) were dissolved in dry DCM (40 mL). The reaction mixture was stirred at room temperature (r.t.) overnight, then it was filtered and the filtrate was evaporated to dryness to afford 4.4 g of crude. The crude was purified by gradient flash chromatography eluting with petroleum ether/EtOAc (from 97/3 to 90/10 v/v) to afford 1-(3′,4′-dichloro-2-fluorobiphenyl-4-yl)cyclopropane carboxylic acid oxiranylmethyl ester (1.0 g, 42.6% yield).

Quelle