Sodium Bicarbonate → HCID 68219039, Verbindung

HRID 241447

Reaktionsgleichung

Reaktionsgleichung von HRID 241447
[F:1][C:2]([F:12])([F:11])[C:3]1[N:8]=[CH:7][C:6]([CH:9]=[O:10])=[CH:5][CH:4]=1.[CH2:13]([Mg]Br)[CH3:14].C([O-])(O)=O.[Na+]>C1COCC1>[F:12][C:2]([F:11])([F:1])[C:3]1[N:8]=[CH:7][C:6]([CH:9]([OH:10])[CH2:13][CH3:14])=[CH:5][CH:4]=1

Komponenten

5

Edukt 3

HCID 516892Sodium BicarbonateHCID 27777626-(Trifluoromethyl)pyridine-3-carboxaldehydeHCID 178418443HCID 178418443, Verbindung

Produkt 1

HCID 68219039HCID 68219039, VerbindungAusbeute 49 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

Dissolve 6-trifluoromethyl-pyridine-3-carboxaldehyde (3.526 g, 20.136 mmol) in THF (50 mL). Add ethylmagnesium bromide (3.0 M in Et2O, 7.38 mL, 22.1 mmol) quickly. Stir 30 minutes. Pour the reaction mixture into a saturated NaHCO3 aqueous solution (100 mL). Extract with EtOAc (3×50 mL). Wash the combined organic extracts with a saturated NaCl aqueous solution (75 mL). Dry the organic extracts over Na2SO4; filter; collect the filtrate; and concentrate the filtrate under reduced pressure. Purify the residue by flash chromatography (Analogix® 40 g @ 40 mL/min) eluting with a gradient of EtOAc/hexanes (5% to 50%) over 30 minutes to give the title compound (2.01 g, 49% yield) as a yellow oil. 1H NMR (400.43 MHz, d6-DMSO) δ 8.66 (d, J=1.6 Hz, 1H), 7.95 (dd, J=1.9, 8.1 Hz, 1H), 7.81 (d, J=8.0 Hz, 1H), 5.47 (d, J=4.5 Hz, 1H), 4.60 (q, J=5.8 Hz, 1H), 1.65-1.59 (m, 2H), 0.79 (t, J=7.4 Hz, 3H).

Aufarbeitung

  1. extractionExtract with EtOAc (3×50 mL)
  2. washWash the combined organic extracts with a saturated NaCl aqueous solution (75 mL)
  3. dry with materialDry the organic extracts over Na2SO4
  4. filtrationfilter
  5. customcollect the filtrate
  6. concentrationand concentrate the filtrate under reduced pressure
  7. customPurify the residue by flash chromatography (Analogix® 40 g @ 40 mL/min)
  8. washeluting with a gradient of EtOAc/hexanes (5% to 50%) over 30 minutes

Quellen und Nachweise

ORD-Eintrag
ord-8c8fa22a41c5438c97d12ef1faa9ee45
Quelldatensatz
uspto-grants-2014_02
Patentnummer
US08648200B2

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