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Methanol → (E)-3-[7-Hydroxy-6-methoxy-3-(3,4,5-trimethoxy-benzoyl)-benzofuran-2-yl]-acrylic acid methyl ester

HRID 218834
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 218834
Br[C:2]1[O:3][C:4]2[C:24]([O:25]C(=O)C)=[C:23]([O:29][CH3:30])[CH:22]=[CH:21][C:5]=2[C:6]=1[C:7](=[O:20])[C:8]1[CH:13]=[C:12]([O:14][CH3:15])[C:11]([O:16][CH3:17])=[C:10]([O:18][CH3:19])[CH:9]=1.[CH3:31][O:32][C:33](=[O:36])[CH:34]=[CH2:35].CO.C(=O)([O-])[O-].[K+].[K+]>C(#N)C.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[CH3:31][O:32][C:33](=[O:36])/[CH:34]=[CH:35]/[C:2]1[O:3][C:4]2[C:24]([OH:25])=[C:23]([O:29][CH3:30])[CH:22]=[CH:21][C:5]=2[C:6]=1[C:7](=[O:20])[C:8]1[CH:9]=[C:10]([O:18][CH3:19])[C:11]([O:16][CH3:17])=[C:12]([O:14][CH3:15])[CH:13]=1
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

7

Edukt 4

HCID 887MethanolHCID 7294Methyl AcrylateHCID 11430Potassium CarbonateHCID 247865602-Bromo-7-acetoxy-3-(3,4,5-trimethoxybenzoyl)-6-methoxybenzofuran

Produkt 1

HCID 24786669(E)-3-[7-Hydroxy-6-methoxy-3-(3,4,5-trimethoxy-benzoyl)-benzofuran-2-yl]-acrylic acid methyl esterAusbeute 37 %

Reagenzien, Katalysatoren, Lösungsmittel

2
HCID 167845palladium(II) acetateKatalysatorHCID 6342AcetonitrileLösungsmittel

Versuchsvorschrift

Mixture of 2-bromo-7-acetoxy-3-(3,4,5-trimethoxybenzoyl)-6-methoxy-benzofuran (50 mg, 0.10 mmol) and methylacrylate (0.5 mL, excess) in a mixture of acetonitrile: TEA; 1 mL:0.5 mL was degassed with nitrogen and palladium acetate (10 mg) was added to it. Reaction mixture was stirred for one hour under nitrogen at reflux, more palladium acetate (15 mg) was added and the refluxing was continued for 7 hours (monitored by tlc). Methanol (1 mL) was added followed by the addition of potassium carbonate (70 mg, 0.51 mmol) and stirring was continued for 1 hour. Solvent was distilled and the crude material was purified over silica gel column (eluent Hexane:diethylether; 1:1) to afford the title compound as yellow crystalline solid (17 mg, 37%); 1H NMR (300 MHz, CDCl3) δ 7.61(d, 1H, J=15.76 Hz), 7.14(s, 2H, benzoyl Hs), 6.98(d, 1H, J=8.64 Hz), 6.89(d, 1H, J=8.69 Hz), 6.81(d, 1H, J=15.78 Hz), 3.96(s, 3H, OMe), 3.95(s, 3H, OMe), 3.81(s, 6H, 2×OMe), 3.77(bs, 3H, OMe).

Aufarbeitung

  1. custom1 mL:0.5 mL was degassed with nitrogen and palladium acetate (10 mg)
  2. additionwas added to it
  3. customReaction mixture
  4. temperatureat reflux
  5. waitthe refluxing was continued for 7 hours
  6. stirringstirring
  7. waitwas continued for 1 hour
  8. distillationSolvent was distilled
  9. customthe crude material was purified over silica gel column (eluent Hexane:diethylether; 1:1)

Quellen und Nachweise

ORD-Eintrag
ord-08d4daf1d9d3408bb3513647d4808e95
Quelldatensatz
uspto-grants-2012_06
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08198466B2

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