反应 #214952

反应方程式

methanol

2,4-dimethyl-3-hydroxymethyl-5-iodothiophene

sodium

→

2,4-dimethyl-3-hydroxymethyl-5-methoxythiophene

反应条件

后处理

1. 1
   温度The reaction mixture was heated to 80°-82° C. (internal temperature) for 20 hrs
2. 2
   温度with vigorous stirring, then cooled
3. 3
   workup.ADDITIONThe cold solution was diluted with 150 ml
4. 4
   过滤of methanol, filtered
5. 5
   workup.ADDITIONpoured into ice water
6. 6
   萃取extracted with ether/hexane (ratio 4:1)
7. 7
   洗涤The organic layers were washed with 5% sodium carbonate solution
8. 8
   其他dried
9. 9
   其他evaporated
10. 10
    其他The residue which resulted
11. 11
    其他was recrystallized from hexane

实验过程

12.0 G. (0.151 mol) of cupric oxide and 12.5 g. (0.0466 mol) of 2,4-dimethyl-3-hydroxymethyl-5-iodothiophene were added to a solution of 12.5 g. (0.543 mol) of sodium in 100 ml. of dry methanol. The reaction mixture was heated to 80°-82° C. (internal temperature) for 20 hrs. with vigorous stirring, then cooled. The cold solution was diluted with 150 ml. of methanol, filtered, poured into ice water and extracted with ether/hexane (ratio 4:1). The organic layers were washed with 5% sodium carbonate solution, dried and evaporated. The residue which resulted was recrystallized from hexane to yield 2,4-dimethyl-3-hydroxymethyl-5-methoxythiophene, m.p. 55°-60° C. This product contained about 10% of 2,4-dimethyl-3-hydroxymethylthiophene which is formed in this reaction by reduction of the iodide. Fraction recrystallization of a sample from hexane yielded pure 2,4-dimethyl-3-hydroxymethyl-5-methylthiophene, m.p. 64°-65° C.

来源