반응 #1148658

반응 방정식

n-BuLi

2-methylfuran

Ethylene oxide

→

5-methyl-2-furanethanol

수율 72.5%

용매

THF

반응 조건

후처리

1. 1
   온도then cooled to 0° C
2. 2
   온도to warm to room temperature overnight
3. 3
   기타After quenching with saturated aqueous NH4Cl
4. 4
   기타the resulting layers were separated
5. 5
   추출the aqueous layer was extracted with Et2O (2×)
6. 6
   건조The combined organic layers were dried over Na2SO4
7. 7
   농축concentrated under reduced pressure
8. 8
   workup.DISTILLATIONDistillation at atmospheric pressure (170-185° C.)

실험 절차

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:

출처