Water → HCID 86585669, compound

HRID 2253327Notes

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

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

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

Sources & evidence

ORD record: ord-fd9ccc11e7084e00acb588d1fcc331f0
Source dataset: uspto-grants-2008_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07323570B2

Reaction notes

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