Water → HCID 86585669, compound

HRID 1348893Notes

Reaction equation

HRID 1348893 reaction equation
[C:1]([O:11][CH2:12][CH3:13])(=[O:10])[CH:2]=[CH:3][CH2:4][C:5]([O:7][CH2:8][CH3:9])=[O:6].[Cl:14][C:15]1[CH:16]=[C:17](I)[CH:18]=[CH:19][CH:20]=1.C([O-])(=O)C.[Na+].O>CN(C=O)C.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[Cl:14][C:15]1[CH:20]=[C:19](/[C:3](/[CH2:4][C:5]([O:7][CH2:8][CH3:9])=[O:6])=[CH:2]/[C:1]([O:11][CH2:12][CH3:13])=[O:10])[CH:18]=[CH:17][CH:16]=1

Participants

7

Reactant 4

HCID 962WaterHCID 122691-Chloro-3-iodobenzeneHCID 748981,5-Diethyl pent-2-enedioateHCID 517045Sodium Acetate

Product 1

HCID 86585669HCID 86585669, compoundYield 20.1%

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of diethyl glutaconate (10.0 g. 53.7 mmol), 3-chloroiodobenzene (11.5 g, 48.2 mmol), sodium acetate (4.40 g, 53.7 mmol) and palladium acetate (1.1 g, 4.9 mmol) in DMF (30 mL) was heated to 100° C., stirred for 21 hours, cooled to room temperature, poured into water, filtered, and extracted with ethyl acetate. The combined extracts were washed with water and brine, dried (MgSO4), filtered, and concentrated. The concentrate was purified by flash column chromatography on silica gel 8:1 hexanes/ethyl acetate to provide 2.88 g (20%) of the desired product. MS (DCI/NH3) m/z 297 (M+H)+; 1H NMR (CDCl3) δ 7.43 (m, 2H), 7.32 (m, 3H), 6.26 (s, 2H), 4.19 (m, 4H), 1.21 (t, 3H), 1.31 (t, 3H).

Workup

  1. temperaturecooled to room temperature
  2. filtrationfiltered
  3. extractionextracted with ethyl acetate
  4. washThe combined extracts were washed with water and brine
  5. dry with materialdried (MgSO4)
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe concentrate was purified by flash column chromatography on silica gel 8:1 hexanes/ethyl acetate

Sources & evidence

ORD record
ord-150cdbb8c5a64941aad7b3491c59687d
Source dataset
uspto-grants-2007_05
Patent number
US07211595B2

Reaction notes

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