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

HRID 591398

Reaktionsgleichung

Reaktionsgleichung von HRID 591398
[CH3:1][O:2][C:3](=[O:16])[CH2:4][C:5]1[C:9]2[C:10]([CH3:15])=[CH:11][C:12]([OH:14])=[CH:13][C:8]=2[S:7][CH:6]=1.[CH3:17][C:18]1[C:23]([CH2:24]O)=[CH:22][CH:21]=[C:20]([C:26]([F:29])([F:28])[F:27])[N:19]=1.C(P(CCCC)CCCC)CCC.C1CCN(C(N=NC(N2CCCCC2)=O)=O)CC1>C1COCC1>[CH3:1][O:2][C:3](=[O:16])[CH2:4][C:5]1[C:9]2[C:10]([CH3:15])=[CH:11][C:12]([O:14][CH2:24][C:23]3[C:18]([CH3:17])=[N:19][C:20]([C:26]([F:29])([F:27])[F:28])=[CH:21][CH:22]=3)=[CH:13][C:8]=2[S:7][CH:6]=1

Komponenten

6

Edukt 4

HCID 13831TributylphosphineHCID 730421,1'-(Azodicarbonyl)dipiperidineHCID 2760122(2-Methyl-6-(trifluoromethyl)pyridin-3-yl)methanolHCID 121001301Methyl(6-hydroxy-4-methyl-1-benzothiophen-3-yl)acetate

Produkt 1

HCID 89775295Methyl(4-methyl-6-((2-methyl-6-(trifluoromethyl)pyridin-3-yl)methoxy)-1-benzothiophen-3-yl)acetateAusbeute 91,6 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a mixture of methyl(6-hydroxy-4-methyl-1-benzothiophen-3-yl)acetate (150 mg) and THF (dry) (5 mL) were added (2-methyl-6-(trifluoromethyl)pyridin-3-yl)methanol (133 mg), tri-n-butylphosphine (0.204 mL) and ADDP (192 mg) at room temperature. The mixture was stirred at room temperature for 4 h. The insoluble material was removed by filtration, and the filtrate was concentrated in vacuo. The residue was purified by silica gel column chromatography (EtOAc/hexane) to give the title compound (238 mg).

Aufarbeitung

  1. customThe insoluble material was removed by filtration
  2. concentrationthe filtrate was concentrated in vacuo
  3. customThe residue was purified by silica gel column chromatography (EtOAc/hexane)

Quellen und Nachweise

ORD-Eintrag
ord-8bfb848d220d41678cd37a795211d878
Quelldatensatz
uspto-grants-2016_01
Patentnummer
US09238639B2

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