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Tributylphosphine → Methyl(4-fluoro-6-((2-methyl-6-(trifluoromethyl)pyridin-3-yl)methoxy)-1-benzothiophen-3-yl)acetate

HRID 591565
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 591565
C(P(CCCC)CCCC)CCC.[CH3:14][C:15]1[C:20]([CH2:21][OH:22])=[CH:19][CH:18]=[C:17]([C:23]([F:26])([F:25])[F:24])[N:16]=1.[CH3:27][O:28][C:29](=[O:42])[CH2:30][C:31]1[C:35]2[C:36]([F:41])=[CH:37][C:38](O)=[CH:39][C:34]=2[S:33][CH:32]=1.C1CCN(C(N=NC(N2CCCCC2)=O)=O)CC1>C1COCC1>[CH3:27][O:28][C:29](=[O:42])[CH2:30][C:31]1[C:35]2[C:36]([F:41])=[CH:37][C:38]([O:22][CH2:21][C:20]3[C:15]([CH3:14])=[N:16][C:17]([C:23]([F:24])([F:26])[F:25])=[CH:18][CH:19]=3)=[CH:39][C:34]=2[S:33][CH:32]=1
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Komponenten

6

Edukt 4

HCID 13831TributylphosphineHCID 730421,1'-(Azodicarbonyl)dipiperidineHCID 2760122(2-Methyl-6-(trifluoromethyl)pyridin-3-yl)methanolHCID 129359611Methyl(4-fluoro-6-hydroxy-1-benzothiophen-3-yl)acetate

Produkt 1

HCID 118667067Methyl(4-fluoro-6-((2-methyl-6-(trifluoromethyl)pyridin-3-yl)methoxy)-1-benzothiophen-3-yl)acetate
Ausbeute 85,8 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a mixture of tri-n-butylphosphine (0.655 mL), (2-methyl-6-(trifluoromethyl)pyridin-3-yl)methanol (167 mg), methyl(4-fluoro-6-hydroxy-1-benzothiophen-3-yl)acetate (210 mg) and THF (dry) (15 mL) was added ADDP (662 mg, 2.62 mmol) 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 chromatography (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 chromatography (EtOAc/hexane)

Quellen und Nachweise

ORD-Eintrag
ord-363270ef8b06459abfeb89f315b7d279
Quelldatensatz
uspto-grants-2016_01
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US09238639B2

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