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Tributylphosphine → Methyl(4-fluoro-6-((1-methyl-3-(trifluoromethyl)-1H-pyrazol-5-yl)methoxy)-1-benzothiophen-3-yl)acetate

HRID 591563
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 591563
C(P(CCCC)CCCC)CCC.[CH3:14][N:15]1[C:19]([CH2:20][OH:21])=[CH:18][C:17]([C:22]([F:25])([F:24])[F:23])=[N:16]1.[CH3:26][O:27][C:28](=[O:41])[CH2:29][C:30]1[C:34]2[C:35]([F:40])=[CH:36][C:37](O)=[CH:38][C:33]=2[S:32][CH:31]=1.C1CCN(C(N=NC(N2CCCCC2)=O)=O)CC1>C1COCC1>[CH3:26][O:27][C:28](=[O:41])[CH2:29][C:30]1[C:34]2[C:35]([F:40])=[CH:36][C:37]([O:21][CH2:20][C:19]3[N:15]([CH3:14])[N:16]=[C:17]([C:22]([F:23])([F:24])[F:25])[CH:18]=3)=[CH:38][C:33]=2[S:32][CH:31]=1
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Komponenten

6

Edukt 4

HCID 13831TributylphosphineHCID 730421,1'-(Azodicarbonyl)dipiperidineHCID 58456726(1-Methyl-3-(trifluoromethyl)-1H-pyrazol-5-yl)methanolHCID 129359611Methyl(4-fluoro-6-hydroxy-1-benzothiophen-3-yl)acetate

Produkt 1

HCID 118667066Methyl(4-fluoro-6-((1-methyl-3-(trifluoromethyl)-1H-pyrazol-5-yl)methoxy)-1-benzothiophen-3-yl)acetate
Ausbeute 74,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a mixture of tri-n-butylphosphine (0.793 mL), (1-methyl-3-(trifluoromethyl)-1H-pyrazol-5-yl)methanol (187 mg), methyl(4-fluoro-6-hydroxy-1-benzothiophen-3-yl)acetate (250 mg) and THF (dry) (15 mL) was added ADDP (801 mg) at room temperature. The mixture was stirred at room temperature for 2 h and then concentrated in vacuo. To the residue was added IPE and the insoluble materials were removed by filtration. The filtrate was concentrated in vacuo. The residue was purified by silica gel column chromatography (NH, EtOAc/hexane) and silica gel column chrothatography (EtOAc/hexane) to give the title compound (310 mg). The crystals were recrystallized from acetone-hexane.

Aufarbeitung

  1. concentrationconcentrated in vacuo
  2. additionTo the residue was added IPE
  3. customthe insoluble materials were removed by filtration
  4. concentrationThe filtrate was concentrated in vacuo
  5. customThe residue was purified by silica gel column chromatography (NH, EtOAc/hexane) and silica gel column chrothatography (EtOAc/hexane)

Quellen und Nachweise

ORD-Eintrag
ord-f73cf3400212418c9d87da9c4c09feab
Quelldatensatz
uspto-grants-2016_01
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US09238639B2

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