Cesium carbonate → HCID 178450706, Verbindung

HRID 1849676Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1849676
[CH3:1][C@H:2]1[CH2:7][CH2:6][C@H:5]([CH2:8][OH:9])[CH2:4][CH2:3]1.[Cl:10][C:11]1[C:12](F)=[CH:13][C:14]([F:24])=[C:15]([CH:23]=1)[C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17].C(=O)([O-])[O-].[Cs+].[Cs+]>CS(C)=O.O>[Cl:10][C:11]1[C:12]([O:9][CH2:8][C@H:5]2[CH2:6][CH2:7][C@H:2]([CH3:1])[CH2:3][CH2:4]2)=[CH:13][C:14]([F:24])=[C:15]([CH:23]=1)[C:16]([O:18][C:19]([CH3:20])([CH3:21])[CH3:22])=[O:17]

Komponenten

6

Edukt 3

HCID 10796Cesium carbonateHCID 58042499Tert-butyl 5-chloro-2,4-difluorobenzoateHCID 178461264HCID 178461264, Verbindung

Produkt 1

HCID 178450706HCID 178450706, VerbindungAusbeute 78 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 679Dimethyl SulfoxideLösungsmittelHCID 962WaterLösungsmittel

Reaktionsbedingungen

Temperatur
70 °C

Versuchsvorschrift

To a solution of trans-(4-methylcyclohexyl)methanol (3.00 g, 23.4 mmol) and tert-butyl 5-chloro-2,4-difluorobenzoate (6.43 g, 25.90 mmol) in anhydrous dimethylsulfoxide (40 mL) was added cesium carbonate (16.11 g, 49.44 mmol). The mixture was heated at 70° C. for 96 hours, and then cooled to ambient temperature; diluted with water (300 mL) and extracted with ethyl acetate (4×100 mL). The combined organic layers were washed with water (100 mL) and brine (100 mL); dried over anhydrous sodium sulfate; filtered and concentrated in vacuo. The residue was purified by column chromatography (0% to 10% ethyl acetate in hexanes gradient) to give the title compound (6.48 g 78%): 1H NMR (300 MHz, CDCl3) δ 7.87 (d, J=7.7 Hz, 1H), 6.61 (d, J=12.3 Hz, 1H), 3.82 (d, J=6.2 Hz, 2H), 1.91-1.73 (m, 8H), 1.56 (s, 9H), 1.17-0.96 (m, 5H).

Aufarbeitung

  1. temperaturecooled to ambient temperature
  2. extractionextracted with ethyl acetate (4×100 mL)
  3. washThe combined organic layers were washed with water (100 mL) and brine (100 mL)
  4. dry with materialdried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified by column chromatography (0% to 10% ethyl acetate in hexanes gradient)

Quellen und Nachweise

ORD-Eintrag
ord-35ed5711d97642cf95628581928abed6
Quelldatensatz
uspto-grants-2015_02
Patentnummer
US08952169B2

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