반응 #60215

반응 방정식

iodobenzene

diethylglutaconate

NaOAc

→

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

수율 28.0%

용매

CH2Cl2

DMA

DMA

반응 조건

후처리

1. 1
   온도the reaction was cooled
2. 2
   세척washed with water (4×10 ml)
3. 3
   세척The organic layer was washed with sat. aq. NaHCO3 (20 ml), brine (20 ml)
4. 4
   건조dried with Na2SO4
5. 5
   여과filtered
6. 6
   농축concentrated under reduced pressure
7. 7
   기타The dark oil was purified by column chromatography
8. 8
   기타The product oil was dried overnight in vacuo

실험 절차

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.

출처