反应 #2844

反应方程式

(5-iodo-thiophene-3-yl)methanol

DMF

→

title compound

4-Hydroxymethyl-thiophene-2-carbonitrile

溶剂

EtOAc

反应条件

后处理

1. 1
   洗涤The resulting solution is washed with 1N NH4OH, H2O and sat. NaCl
2. 2
   干燥The organic layer is dried over MgSO4
3. 3
   过滤filtered
4. 4
   浓缩concentrated
5. 5
   其他The crude product is purified by column chromatography
6. 6
   洗涤eluting with gradient of 20% EtOAc/hexanes to 30% EtOAc/hexanes

实验过程

To a solution of (5-iodo-thiophene-3-yl)methanol (42 g, 176 mmol) in 150 mL of DMF is added zinc cyanide (12.4 g, 106 mmol) and tetrakis(triphenylphospine)palladium (0) (8.13 g, 7.04 mmol). The solution is heated to 80° C. After 6 h, the solution is diluted with 3 L of EtOAc. The resulting solution is washed with 1N NH4OH, H2O and sat. NaCl. The organic layer is dried over MgSO4, filtered and concentrated. The crude product is purified by column chromatography eluting with gradient of 20% EtOAc/hexanes to 30% EtOAc/hexanes to afford the title compound (10 g, 72 mmol) as a clear oil.

来源