Dimethyl Sulfoxide → Methyl 5-(4-hydroxytetrahydrofuran-3-yloxy)-4'-methylbiphenyl-3-carboxylate

HRID 1845325Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1845325
[OH:1][C:2]1[CH:3]=[C:4]([C:15]([O:17][CH3:18])=[O:16])[CH:5]=[C:6]([C:8]2[CH:13]=[CH:12][C:11]([CH3:14])=[CH:10][CH:9]=2)[CH:7]=1.C(=O)([O-])[O-].[K+].[K+].CS(C)=O.[CH:29]12[O:34][CH:33]1[CH2:32][O:31][CH2:30]2>CCOC(C)=O>[OH:34][CH:29]1[CH2:30][O:31][CH2:32][CH:33]1[O:1][C:2]1[CH:3]=[C:4]([C:15]([O:17][CH3:18])=[O:16])[CH:5]=[C:6]([C:8]2[CH:9]=[CH:10][C:11]([CH3:14])=[CH:12][CH:13]=2)[CH:7]=1

Komponenten

6

Edukt 4

HCID 679Dimethyl SulfoxideHCID 11430Potassium CarbonateHCID 675113,6-Dioxabicyclo[3.1.0]hexaneHCID 58187967Methyl 5-hydroxy-4'-methyl-[1,1'-biphenyl]-3-carboxylate

Produkt 1

HCID 58188331Methyl 5-(4-hydroxytetrahydrofuran-3-yloxy)-4'-methylbiphenyl-3-carboxylate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8857Ethyl AcetateLösungsmittel

Reaktionsbedingungen

Temperatur
110 °C

Versuchsvorschrift

A stirred mixture of methyl 5-hydroxy-4′-methylbiphenyl-3-carboxylate (370 mg, 1.4 mmol), potassium carbonate (421 mg, 3.05 mmol), DMSO (8 mL), and 3,6-dioxabicyclo[3.1.0]hexane (260 mg, 3.0 mmol) was heated at 110° C. overnight. After cooling, the reaction mixture was diluted with EtOAc. The organic phase was washed with aq. NaHCO3 (sat.), dried over anhydrous MgSO4, filtered, and concentrated. The residue was purified by flash chromatography to afford the title compound.

Aufarbeitung

  1. temperatureAfter cooling
  2. washThe organic phase was washed with aq. NaHCO3 (sat.)
  3. dry with materialdried over anhydrous MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe residue was purified by flash chromatography

Quellen und Nachweise

ORD-Eintrag
ord-97cc728651fb49dcb451a4f899c04298
Quelldatensatz
uspto-grants-2015_02
Patentnummer
US08946439B2

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