Reacción #1148659

Ecuación de reacción

NH4Cl

n-BuLi

2-ethylfuran

Ethylene oxide

→

2v(1)

Rendimiento 80.2%

2-Ethyl-5-(2-hydroxyethyl)furan

Rendimiento 80.2%

Disolventes

THF

Condiciones de reacción

Tratamiento posterior

1. 1
   workup.STIRRINGThe reaction was stirred for 0.5 h at −15° C. and overnight at rt
2. 2
   Extracciónthe mixture was extracted with ether (3×)
3. 3
   LavadoThe combined extracts were washed with water (1×) and brine (1×)
4. 4
   Secadodried over Na2SO4
5. 5
   OtroPurification by flash chromatography on silica gel eluting with 30% EtOAc/70% hexane

Procedimiento

n-BuLi (2.5 M in hexane, 4.4 mL, 11 mmol) was added to a solution of 2-ethylfuran (1.05 mL, 10 mmol) in THF (10 mL) at −25° C. The solution was warmed to rt and stirred for 3 h. Ethylene oxide (0.75 mL) was added at −78° C. The reaction was stirred for 0.5 h at −15° C. and overnight at rt. Aqueous sat. NH4Cl was added and the mixture was extracted with ether (3×). The combined extracts were washed with water (1×) and brine (1×) and dried over Na2SO4. Purification by flash chromatography on silica gel eluting with 30% EtOAc/70% hexane gave 1.12 g (8.02 mmol, 80.2%) of 2v(1) as a yellow oil.

Fuente