Reaktion #60215

Reaktionsgleichung

iodobenzene

diethylglutaconate

NaOAc

→

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

Ausbeute 28.0%

Lösungsmittel

CH2Cl2

DMA

DMA

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturthe reaction was cooled
2. 2
   Waschenwashed with water (4×10 ml)
3. 3
   WaschenThe organic layer was washed with sat. aq. NaHCO3 (20 ml), brine (20 ml)
4. 4
   Trocknendried with Na2SO4
5. 5
   Filtrationfiltered
6. 6
   Einengenconcentrated under reduced pressure
7. 7
   SonstigeThe dark oil was purified by column chromatography
8. 8
   SonstigeThe product oil was dried overnight in vacuo

Vorschrift

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.

Quelle