Potassium Carbonate → Benzyl 4-{(E)-2-[4-((E)-2-methoxycarbonylvinyl)-2,6-dimethylphenyl]-vinyl}-3-nitrobenzoate

HRID 1513282Notes

Reaction equation

[CH2:1]([O:8][C:9](=[O:21])[C:10]1[CH:15]=[CH:14][C:13]([CH2:16]Br)=[C:12]([N+:18]([O-:20])=[O:19])[CH:11]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:22]1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.COC1C=CC(NC2OC(C3C=CC4N=[C:61]([C:63]5[C:68]([CH3:69])=[CH:67][C:66]([CH2:70][CH2:71][C:72]([OH:74])=[O:73])=[CH:65][C:64]=5[CH3:75])NC=4C=3)=NN=2)=CC=1.C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C.C(OCC)(=O)C>[CH3:22][O:74][C:72](/[CH:71]=[CH:70]/[C:66]1[CH:67]=[C:68]([CH3:69])[C:63](/[CH:61]=[CH:16]/[C:13]2[CH:14]=[CH:15][C:10]([C:9]([O:8][CH2:1][C:2]3[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=3)=[O:21])=[CH:11][C:12]=2[N+:18]([O-:20])=[O:19])=[C:64]([CH3:75])[CH:65]=1)=[O:73]

Participants

Conditions

Temperature: 100 °C

Procedure

A mixture of 4-bromomethyl-3-nitrobenzoic acid benzyl ester (2.06 g, 5.88 mmol) and triphenylphosphine (1.54 g, 5.87 mmol) in DMF (10 mL) was heated at 100° C. for 1 h. To this solution was then added 3-(4-formyl-3,5-dimethylphenyl)-acrylic acid methyl ester (1.28 g, 5.86 mmol) (Example 1-60, step C) and potassium carbonate (1.63 g, 11.8 mmol) and the mixture was stirred for at 100° C. 18 h. The mixture was poured into ethyl acetate and extracted with water once and brine five times. The organic layer was dried, filtered, and solvent removed under reduced pressure. The residue was purified by chromatography using a 0-40% gradient of heptane/ethyl acetate to give the title compound.

Workup

custom18 h
extractionextracted with water once
customThe organic layer was dried
filtrationfiltered
customsolvent removed under reduced pressure
customThe residue was purified by chromatography

Sources & evidence

ORD record: ord-554665f2053e48cc9ef2ff06c0558e0c
Source dataset: uspto-grants-2012_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08217065B2

Reaction notes

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