Reacción #163418

Ecuación de reacción

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

Rendimiento 42.7%

Disolventes

DCM

Condiciones de reacción

Tratamiento posterior

1. 1
   Filtraciónit was filtered
2. 2
   Otrothe filtrate was evaporated to dryness
3. 3
   Otroto afford 4.4 g of crude
4. 4
   OtroThe crude was purified by gradient flash chromatography
5. 5
   Lavadoeluting with petroleum ether/EtOAc (from 97/3 to 90/10 v/v)

Procedimiento

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).

Fuente