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Pivalic acid → (E)-methyl 3-(4-((2-(2-isopropylphenyl)-6-methoxybenzo[b]thiophen-3-yl)oxy)phenyl)acrylate

HRID 632685
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 632685
[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]2[C:10]([O:11][C:12]3[CH:17]=[CH:16][C:15](/[CH:18]=[CH:19]/[C:20](=[O:22])C)=[CH:14][CH:13]=3)=[CH:9][S:8][C:7]=2[CH:23]=1.I[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=1[CH:31]([CH3:33])[CH3:32].CC(C)(C)[C:36](O)=[O:37].C(=O)([O-])[O-].[K+].[K+]>CC(N(C)C)=O.CCOC(C)=O>[CH:31]([C:26]1[CH:27]=[CH:28][CH:29]=[CH:30][C:25]=1[C:9]1[S:8][C:7]2[CH:23]=[C:3]([O:2][CH3:1])[CH:4]=[CH:5][C:6]=2[C:10]=1[O:11][C:12]1[CH:17]=[CH:16][C:15](/[CH:18]=[CH:19]/[C:20]([O:37][CH3:36])=[O:22])=[CH:14][CH:13]=1)([CH3:33])[CH3:32]
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

7

Edukt 4

HCID 6417Pivalic acidHCID 11430Potassium CarbonateHCID 87931o-IodocumeneHCID 118574934(E)-4-(4-((6-methoxybenzo [b]thiophen-3-yl)oxy)phenyl)but-3-en-2-one

Produkt 1

HCID 86730642(E)-methyl 3-(4-((2-(2-isopropylphenyl)-6-methoxybenzo[b]thiophen-3-yl)oxy)phenyl)acrylateAusbeute 77,7 %

Reagenzien, Katalysatoren, Lösungsmittel

2
HCID 8857Ethyl AcetateLösungsmittelHCID 31374DimethylacetamideLösungsmittel

Reaktionsbedingungen

Temperatur
140 °C

Versuchsvorschrift

To a solution of (E)-4-(4-((6-methoxybenzo[b]thiophen-3-yl)oxy)phenyl)but-3-en-2-one (45 g, 132 mmol) in anhydrous DMA (450 mL) at room temperature was added 1-iodo-2-isopropylbenzene (57 g, 231.6 mmol), chloro[2-(dicyclohexylphosphino)-3,6-dimethoxy-2′,4′,6′-tri-i-propyl-1,1′-biphenyl][2-(2-aminoethyl)phenyl]palladium(II) (BrettPhos Palladacycle 1st generation, 6.34 g, 7.93 mmol), trimethylacetic acid (40.5 g, 397 mmol) and potassium carbonate (55 g, 397 mmol). The resulting mixture was heated at 140° C. for 1.5 hours. The reaction mixture was cooled down to 50° C. The reaction was diluted with EtOAc (400 mL) and let to cool down to room temperature. As the reaction cooled, a precipitate formed and was removed by filtration. The mother liquor was washed with water and brine, dried over anhydrous Na2SO4, filtered and concentrated in vacuo to give the crude product, which was purified by column chromatography (SiO2, 10-20% EtOAc/heptane) to afford (E)-methyl 3-(4-((2-(2-isopropylphenyl)-6-methoxybenzo[b]thiophen-3-yl)oxy)phenyl)acrylate (47 g, 102.5 mmol). 1H NMR (400 MHz, CDCl3) δ ppm=7.61 (d, J=15.9 Hz, 1H), 7.42-7.29 (m, 7H), 7.15 (ddd, J=8.1, 5.7, 2.8 Hz, 1H), 6.97 (dd, J=8.8, 2.3 Hz, 1H), 6.91-6.85 (m, 2H), 6.29 (d, J=16.0 Hz, 1H), 3.91 (s, 3H), 3.80 (s, 3H), 3.26 (p, J=6.8 Hz, 1H), 1.19 (d, J=6.9 Hz, 6H), LC/MS (m/z, MH+): 459.5.

Aufarbeitung

  1. temperatureThe reaction mixture was cooled down to 50° C
  2. temperatureto cool down to room temperature
  3. temperatureAs the reaction cooled
  4. customa precipitate formed
  5. customwas removed by filtration
  6. washThe mother liquor was washed with water and brine
  7. dry with materialdried over anhydrous Na2SO4
  8. filtrationfiltered
  9. concentrationconcentrated in vacuo
  10. customto give the crude product, which
  11. customwas purified by column chromatography (SiO2, 10-20% EtOAc/heptane)

Quellen und Nachweise

ORD-Eintrag
ord-7c697243bc054170a42e26e96cc30eb3
Quelldatensatz
uspto-grants-2016_04
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US09321746B2

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