تفاعل #60215

معادلة التفاعل

iodobenzene

diethylglutaconate

NaOAc

→

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

المردود 28.0%

المذيبات

CH2Cl2

DMA

DMA

ظروف التفاعل

المعالجة

1. 1
   درجة الحرارةthe reaction was cooled
2. 2
   غسيلwashed with water (4×10 ml)
3. 3
   غسيلThe organic layer was washed with sat. aq. NaHCO3 (20 ml), brine (20 ml)
4. 4
   تجفيفdried with Na2SO4
5. 5
   ترشيحfiltered
6. 6
   تركيزconcentrated under reduced pressure
7. 7
   أخرىThe dark oil was purified by column chromatography
8. 8
   أخرىThe product oil was dried overnight in vacuo

الإجراء التجريبي

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.

المصدر