Hydrochloric Acid → HCID 86703748, Verbindung
Reaktionsgleichung
[CH3:1][CH:2]1[CH2:7][CH2:6][CH2:5][CH:4]([CH3:8])[CH:3]1[CH2:9][OH:10].C(=O)([O-])[O-].[Cs+].[Cs+].[Cl:17][C:18]1[C:19](F)=[CH:20][C:21]([F:31])=[C:22]([CH:30]=1)[C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24].Cl>CS(C)=O>[Cl:17][C:18]1[C:19]([O:10][CH2:9][CH:3]2[CH:4]([CH3:8])[CH2:5][CH2:6][CH2:7][CH:2]2[CH3:1])=[CH:20][C:21]([F:31])=[C:22]([CH:30]=1)[C:23]([O:25][C:26]([CH3:27])([CH3:28])[CH3:29])=[O:24]Komponenten
Reaktionsbedingungen
- Temperatur
- 70 °C
Versuchsvorschrift
To a solution of (2,6-dimethylcyclohexyl)methanol (0.34 g, 2.40 mmol) in anhydrous dimethylsulfoxide (5 mL) were added cesium carbonate (1.56 g, 4.80 mmol) and tert-butyl 5-chloro-2,4-difluorobenzoate (0.53 g, 2.16 mmol) and the reaction mixture was stirred at 70° C. for 16 hours. The reaction mixture was cooled down and acidified to pH=1 with 5% aqueous hydrochloric acid solution and extracted with ethyl acetate (2×15 mL), the combined organics were washed with brine (15 mL); dried over anhydrous sodium sulfate, filtered and concentrated in vacuo. Purification of the residue by column chromatography (0 to 10% ethyl acetate in hexanes) afforded the title compound (0.43 g, 54%): MS (ES+) m/z 317.2, 315.2 (M−54); MS (ES−) m/z 315.1, 313.1, (M−56).
Aufarbeitung
- temperatureThe reaction mixture was cooled down
- extractionextracted with ethyl acetate (2×15 mL)
- washthe combined organics were washed with brine (15 mL)
- dry with materialdried over anhydrous sodium sulfate
- filtrationfiltered
- concentrationconcentrated in vacuo
- customPurification of the residue by column chromatography (0 to 10% ethyl acetate in hexanes)
Quellen und Nachweise
- ORD-Eintrag
- ord-1a8ae6534a0b4a0db1873e1fc0e1b6bb
- Quelldatensatz
- uspto-grants-2015_02
- Patentnummer
- US08952169B2
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