Cesium carbonate → HCID 86703465, Verbindung

HRID 1849609Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1849609
[CH3:1][C:2]1([CH2:8][OH:9])[CH2:7][CH2:6][CH2:5][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>[Cl:10][C:11]1[C:12]([O:9][CH2:8][C:2]2([CH3:1])[CH2:7][CH2:6][CH2:5][CH2:4][CH2:3]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

5

Edukt 3

HCID 10796Cesium carbonateHCID 1501840(1-Methylcyclohexyl)methanolHCID 58042499Tert-butyl 5-chloro-2,4-difluorobenzoate

Produkt 1

HCID 86703465HCID 86703465, VerbindungAusbeute 45,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 679Dimethyl SulfoxideLösungsmittel

Reaktionsbedingungen

Temperatur
70 °C

Versuchsvorschrift

To a solution of (1-methylcyclohexyl)methanol (4.98 g, 38.80 mmol) and tert-butyl 5-chloro-2,4-difluorobenzoate (20.67 g, 83.10 mmol) in anhydrous dimethylsulfoxide (80 mL) was added cesium carbonate (25.14 g, 77.20 mmol). The mixture was heated to 70° C. and stirred for 16 hours. The mixture was then cooled to ambient temperature, filtered through a pad of diatomaceous earth and the solid was washed with ethyl acetate. The combined organic layers were washed with water and brine; dried over anhydrous sodium sulfate, filtered and concentrated in vacuo. The residue was purified by column chromatography (0% to 10% ethyl acetate in hexanes) to afford the title compound (6.26 g, 44%): 1H NMR (300 MHz, CDCl3) δ 7.87 (d, J=7.7 Hz, 1H), 6.62 (d, J=12.2 Hz, 1H), 3.70 (s, 2H), 1.57 (s, 9 H), 1.52-1.31 (m, 10H), 1.08 (s, 3H).

Aufarbeitung

  1. temperatureThe mixture was then cooled to ambient temperature
  2. filtrationfiltered through a pad of diatomaceous earth
  3. washthe solid was washed with ethyl acetate
  4. washThe combined organic layers were washed with water and brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customThe residue was purified by column chromatography (0% to 10% ethyl acetate in hexanes)

Quellen und Nachweise

ORD-Eintrag
ord-fc71d238551e40d2b711cca7e8d49b5f
Quelldatensatz
uspto-grants-2015_02
Patentnummer
US08952169B2

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