Sodium hydride → 1-(2,2,2-trifluoroethyl)-1H-pyrazole-4-carbaldehyde

HRID 220485Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 220485
[NH:1]1[CH:5]=[C:4]([CH:6]=[O:7])[CH:3]=[N:2]1.[H-].[Na+].[F:10][C:11]([F:25])([F:24])[CH2:12]OS(C1C=CC(C)=CC=1)(=O)=O>CN(C=O)C>[F:10][C:11]([F:25])([F:24])[CH2:12][N:1]1[CH:5]=[C:4]([CH:6]=[O:7])[CH:3]=[N:2]1

Komponenten

5

Edukt 3

HCID 24758Sodium hydrideHCID 67942Ethanol, 2,2,2-trifluoro-, 1-(4-methylbenzenesulfonate)HCID 51306731H-pyrazole-4-carbaldehyde

Produkt 1

HCID 196195521-(2,2,2-trifluoroethyl)-1H-pyrazole-4-carbaldehyde

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel3×

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

Add 1H-pyrazole-4-carbaldehyde (0.400 g, 4.16 mmol) as a solution in DMF (2 mL) dropwise to a suspension of sodium hydride (0.333 g, 8.32 mmol) in DMF (5 mL) at 0° C. Stir for 15 min. at 0° C. Add 2,2,2-trifluoroethyl-p-toluenesulfonate (1.27 g, 5.00 mmol) and DMF (3 mL) to the reaction mixture. Heat to 60° C. for 18 hr. Quench with aqueous saturated sodium bicarbonate solution and add ethyl acetate. Separate organic layer. Extract aqueous layer twice with ethyl acetate, wash combined organics with brine, dry (magnesium sulfate), filter, concentrate and purify (silica gel chromatography, eluting with 0:100 to 100:0 ethyl acetate:hexanes) to give the title preparation (309 mg, 42%). GC-MS: m/z=178 [M+].

Aufarbeitung

  1. temperatureHeat to 60° C. for 18 hr
  2. customQuench with aqueous saturated sodium bicarbonate solution
  3. additionadd ethyl acetate
  4. washExtract aqueous layer twice with ethyl acetate, wash
  5. dry with materialdry (magnesium sulfate)
  6. filtrationfilter
  7. concentrationconcentrate
  8. custompurify
  9. wash(silica gel chromatography, eluting with 0:100 to 100:0 ethyl acetate:hexanes)
  10. customto give the title
  11. custompreparation (309 mg, 42%)

Quellen und Nachweise

ORD-Eintrag
ord-20a3258226dc44fda1b718e3a563a5b0
Quelldatensatz
uspto-grants-2012_06
Patentnummer
US08202873B2

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