反应 #60215

反应方程式

iodobenzene

diethylglutaconate

NaOAc

→

diethyl (2Z)-3-phenylpent-2-ene-1,5-dioate

收率 28.0%

溶剂

CH2Cl2

DMA

DMA

反应条件

后处理

1. 1
   温度the reaction was cooled
2. 2
   洗涤washed with water (4×10 ml)
3. 3
   洗涤The organic layer was washed with sat. aq. NaHCO3 (20 ml), brine (20 ml)
4. 4
   干燥dried with Na2SO4
5. 5
   过滤filtered
6. 6
   浓缩concentrated under reduced pressure
7. 7
   其他The dark oil was purified by column chromatography
8. 8
   其他The product oil was dried overnight in vacuo

实验过程

A solution of iodobenzene (1.08 ml, 9.67 mmol) in DMA (5 ml) was added dropwise to a solution of diethylglutaconate (2 g, 10.74 mmol), Pd(OAc)2 (250 mg, 1.07 mmol), NaOAc (880 mg, 10.74 mmol) in DMA (5 ml) at 115° C. under argon. After heating for 8 hours at 130° C., the reaction was cooled, diluted with CH2Cl2 (60 ml), and washed with water (4×10 ml). The organic layer was washed with sat. aq. NaHCO3 (20 ml), brine (20 ml), dried with Na2SO4, filtered, and concentrated under reduced pressure. The dark oil was purified by column chromatography using CH2Cl2 as the eluent. The product oil was dried overnight in vacuo giving diethyl (2Z)-3-phenylpent-2-ene-1,5-dioate in 28% yield.

来源