Tributylphosphine → Methyl(4-chloro-6-((2,6-dimethylpyridin-3-yl)methoxy)-1-benzothiophen-3-yl)acetate

HRID 591404Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 591404
[CH3:1][O:2][C:3](=[O:16])[CH2:4][C:5]1[C:9]2[C:10]([Cl: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]([CH3:26])[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]([Cl:15])=[CH:11][C:12]([O:14][CH2:24][C:23]3[C:18]([CH3:17])=[N:19][C:20]([CH3:26])=[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 2784752(2,6-Dimethylpyridin-3-yl)methanolHCID 20770824Methyl(4-chloro-6-hydroxy-1-benzothiophen-3-yl)acetate

Produkt 1

HCID 118667003Methyl(4-chloro-6-((2,6-dimethylpyridin-3-yl)methoxy)-1-benzothiophen-3-yl)acetateAusbeute 86,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a mixture of methyl(4-chloro-6-hydroxy-1-benzothiophen-3-yl)acetate (110 mg) and THF (dry) (5 mL) were added (2,6-dimethylpyridin-3-yl)methanol (58.8 mg), tri-n-butylphosphine (0.159 mL) and ADDP (130 mg) at room temperature. The mixture was stirred at room temperature for 12 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 (139 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-6424d72e73ff413e9cee9a4d934d15a4
Quelldatensatz
uspto-grants-2016_01
Patentnummer
US09238639B2

Notizen zur Reaktion

Wird geladen…