Reaktion #428748

Reaktionsgleichung

Sodium hydride

Sodium hydride

2,2,2-trifluoroethanol

Sodium hydride

5-Chloromethylfuran-2-carboxylic acid methyl ester

→

title compound

Ausbeute 48.0%

5-(2,2,2-Trifluoroethoxymethyl)-furan-2-carboxylic acid

Ausbeute 48.0%

Lösungsmittel

EtOAc

DMF

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.STIRRINGthe mixture was stirred at room temperature for 18 h
2. 2
   workup.WAITat 60 C for 3 h
3. 3
   workup.WAITat 100 C for 3 h
4. 4
   workup.STIRRINGthe reaction mixture was stirred at room temperature for 18 h
5. 5
   workup.STIRRINGthe mixture was stirred at room temperature for 3 h
6. 6
   Waschenthen washed with saturated aq. sodium bicarbonate (4×6 mL), saturated aq. ammonium chloride (2×6 mL)
7. 7
   ExtraktionThe aqueous extractions
8. 8
   workup.ADDITIONbrought to pH 1 by the addition of 2M HCl
9. 9
   Extraktionextracted with DCM (5 mL)
10. 10
    ExtraktionThe combined organic extractions
11. 11
    Waschenwere washed with water (3×6 mL)
12. 12
    Trocknenbrine (6 mL) and then dried over sodium sulfate
13. 13
    Sonstigeevaporated under vacuum

Vorschrift

Sodium hydride (60% dispersion in mineral oil, 60 mg, 1.50 mmol) was added to 2,2,2-trifluoroethanol (99 μL, 1.38 mmol) in anhydrous DMF (1 mL) and the mixture was stirred under nitrogen for 20 min. 5-Chloromethylfuran-2-carboxylic acid methyl ester (200 mg, 1.15 mmol) was then added and the mixture was stirred at room temperature for 18 h, then at 60 C for 3 h, then at 100 C for 3 h. Sodium hydride (60% dispersion in mineral oil, 30 mg, 0.75 mmol) was added under nitrogen and the reaction mixture was stirred at room temperature for 18 h. Sodium hydride (60% dispersion in mineral oil, 30 mg, 0.75 mmol) was added and the mixture was stirred at room temperature for 3 h. The reaction mixture was diluted with EtOAc (30 mL) then washed with saturated aq. sodium bicarbonate (4×6 mL), saturated aq. ammonium chloride (2×6 mL) and then brine (6 mL). The aqueous extractions were combined and brought to pH 1 by the addition of 2M HCl and then extracted with DCM (5 mL). The combined organic extractions were washed with water (3×6 mL), then brine (6 mL) and then dried over sodium sulfate and evaporated under vacuum to afford the title compound (123 mg, 48%), which was used without further purification. Method C HPLC-MS: (MH+) requires m/z=225. Found: m/z=252, Rt=1.15 min (97%).

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