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

HRID 1513282
Notes
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Reaction equation

HRID 1513282 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]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 11430Potassium CarbonateHCID 11776TriphenylphosphineHCID 252354053-(4-{6-[5-(4-Methoxyphenylamino)-[1,3,4]oxadiazol-2-yl]-1H-benzoimidazol-2-yl}-3,5-dimethylphenyl)-propionic acidHCID 66965750Benzyl 4-bromomethyl-3-nitrobenzoate

Product 1

HCID 66966058Benzyl 4-{(E)-2-[4-((E)-2-methoxycarbonylvinyl)-2,6-dimethylphenyl]-vinyl}-3-nitrobenzoate

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

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

  1. custom18 h
  2. extractionextracted with water once
  3. customThe organic layer was dried
  4. filtrationfiltered
  5. customsolvent removed under reduced pressure
  6. 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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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes