Iodobenzene → diethyl (2Z)-3-phenylpent-2-ene-1,5-dioate
Reaction equation
I[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:8]([O:10][C:11](=[O:20])[CH:12]=[CH:13][CH2:14][C:15]([O:17][CH2:18][CH3:19])=[O:16])[CH3:9].CC([O-])=O.[Na+]>CC(N(C)C)=O.C(Cl)Cl.CC([O-])=O.CC([O-])=O.[Pd+2]>[C:2]1(/[C:13](/[CH2:12][C:11]([O:10][CH2:8][CH3:9])=[O:20])=[CH:14]\[C:15]([O:17][CH2:18][CH3:19])=[O:16])[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1Participants
7
Reactant 3
Product 1
Reagents, catalysts & solvents 3
Conditions
- Temperature
- 130 °C
Procedure
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.
Workup
- temperaturethe reaction was cooled
- washwashed with water (4×10 ml)
- washThe organic layer was washed with sat. aq. NaHCO3 (20 ml), brine (20 ml)
- dry with materialdried with Na2SO4
- filtrationfiltered
- concentrationconcentrated under reduced pressure
- customThe dark oil was purified by column chromatography
- customThe product oil was dried overnight in vacuo
Sources & evidence
- ORD record
- ord-46d90c30057e44fa9c533d29c67dcbb9
- Source dataset
- uspto-grants-2008_09
- Patent number
- US07425557B2
Reaction notes
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