تفاعل #1148658

معادلة التفاعل

n-BuLi

2-methylfuran

Ethylene oxide

→

5-methyl-2-furanethanol

المردود 72.5%

المذيبات

THF

ظروف التفاعل

المعالجة

1. 1
   درجة الحرارةthen cooled to 0° C
2. 2
   درجة الحرارةto warm to room temperature overnight
3. 3
   أخرىAfter quenching with saturated aqueous NH4Cl
4. 4
   أخرىthe resulting layers were separated
5. 5
   استخلاصthe aqueous layer was extracted with Et2O (2×)
6. 6
   تجفيفThe combined organic layers were dried over Na2SO4
7. 7
   تركيزconcentrated under reduced pressure
8. 8
   workup.DISTILLATIONDistillation at atmospheric pressure (170-185° C.)

الإجراء التجريبي

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:

المصدر