Reacción #1148658

Ecuación de reacción

n-BuLi

2-methylfuran

Ethylene oxide

→

5-methyl-2-furanethanol

Rendimiento 72.5%

Disolventes

THF

Condiciones de reacción

Tratamiento posterior

1. 1
   Temperaturathen cooled to 0° C
2. 2
   Temperaturato warm to room temperature overnight
3. 3
   OtroAfter quenching with saturated aqueous NH4Cl
4. 4
   Otrothe resulting layers were separated
5. 5
   Extracciónthe aqueous layer was extracted with Et2O (2×)
6. 6
   SecadoThe combined organic layers were dried over Na2SO4
7. 7
   Concentraciónconcentrated under reduced pressure
8. 8
   workup.DISTILLATIONDistillation at atmospheric pressure (170-185° C.)

Procedimiento

A solution of n-BuLi (83 mL, 133.0 mmol, 1.2 eq, 1.6 M in hexanes) was added to a stirred solution of 2-methylfuran (10 mL, 110.8 mmol, 1 eq) in THF (85 mL) at 0° C. under inert atmosphere. The reaction mixture was stirred for 4 h at room temperature then cooled to 0° C. Ethylene oxide (8.3 mL, 166.3 mmol, 1.5 eq) was added dropwise and the reaction mixture was allowed to warm to room temperature overnight. After quenching with saturated aqueous NH4Cl, the resulting layers were separated and the aqueous layer was extracted with Et2O (2×). The combined organic layers were dried over Na2SO4 and concentrated under reduced pressure. Distillation at atmospheric pressure (170-185° C.) gave 10.13 g (80.3 mmol, 72%) of 5-methyl-2-furanethanol (2f(2)) as a light yellow oil:

Fuente