反応 #1148658

反応方程式

n-BuLi

2-methylfuran

Ethylene oxide

→

5-methyl-2-furanethanol

収率 72.5%

溶媒

THF

反応条件

後処理

1. 1
   温度then cooled to 0° C
2. 2
   温度to warm to room temperature overnight
3. 3
   その他After quenching with saturated aqueous NH4Cl
4. 4
   その他the resulting layers were separated
5. 5
   抽出the aqueous layer was extracted with Et2O (2×)
6. 6
   乾燥The combined organic layers were dried over Na2SO4
7. 7
   濃縮concentrated under reduced pressure
8. 8
   workup.DISTILLATIONDistillation at atmospheric pressure (170-185° C.)

実験手順

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:

出典