Reaktionsgleichung
[I:1][C:2]1[CH:11]=[C:6]([C:7]([O:9][CH3:10])=[O:8])[C:5]([OH:12])=[CH:4][CH:3]=1.N1C=CN=C1.Cl[Si:19]([CH:26]([CH3:28])[CH3:27])([CH:23]([CH3:25])[CH3:24])[CH:20]([CH3:22])[CH3:21]>CN(C=O)C>[CH3:10][O:9][C:7](=[O:8])[C:6]1[CH:11]=[C:2]([I:1])[CH:3]=[CH:4][C:5]=1[O:12][Si:19]([CH:26]([CH3:28])[CH3:27])([CH:23]([CH3:25])[CH3:24])[CH:20]([CH3:22])[CH3:21]Komponenten
5
Edukt 3
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 1
Versuchsvorschrift
A solution of methyl 5-iodosalicylate (2.00 g, 7.20 mmol) in DMF (20 mL) was treated with imidazole (1.22 g, 18.0 mmol) then chlorotriisopropylsilane (1.85 mL, 8.60 mmol). The mixture was stirred at RT for 18 h. The mixture was evaporated in vacuo and the residue was partitioned between EtOAc and water. The aqueous layer was then extracted with EtOAc (2×). The combined organic layers were washed with a 10% aqueous citric acid solution, 1N aqueous NaOH solution and brine, dried (Na2SO4), filtered and evaporated in vacuo. The residue was purified by FCC, using 0-10% EtOAc in cyclohexane, to give the title compound as a colorless oil (2.88 g, 92%). LCMS (Method 3): Rt 5.72 min, m/z 435 [MH+].
Aufarbeitung
- customThe mixture was evaporated in vacuo
- customthe residue was partitioned between EtOAc and water
- extractionThe aqueous layer was then extracted with EtOAc (2×)
- washThe combined organic layers were washed with a 10% aqueous citric acid solution, 1N aqueous NaOH solution and brine
- dry with materialdried (Na2SO4)
- filtrationfiltered
- customevaporated in vacuo
- customThe residue was purified by FCC
Quellen und Nachweise
- ORD-Eintrag
- ord-d2b657b18bee487ca61d7522a786f771
- Quelldatensatz
- uspto-grants-2016_09
- Patentnummer
- US09440974B2
Verknüpfte Notizen
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