Реакция #60215

Уравнение реакции

iodobenzene

diethylglutaconate

NaOAc

→

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

Выход 28.0%

Растворители

CH2Cl2

DMA

DMA

Условия реакции

Обработка

1. 1
   Температураthe reaction was cooled
2. 2
   Промывкаwashed with water (4×10 ml)
3. 3
   ПромывкаThe organic layer was washed with sat. aq. NaHCO3 (20 ml), brine (20 ml)
4. 4
   Сушкаdried with Na2SO4
5. 5
   Фильтрацияfiltered
6. 6
   Концентрированиеconcentrated under reduced pressure
7. 7
   ДругоеThe dark oil was purified by column chromatography
8. 8
   ДругоеThe product oil was dried overnight in vacuo

Методика

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.

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