Dimethylformamide → 3-Chloro-2-formylpyridine

HRID 7157

Reaktionsgleichung

Reaktionsgleichung von HRID 7157
CN(CCN(C)C)C.C([Li])CCC.[Cl:14][C:15]1[CH:16]=[N:17][CH:18]=[CH:19][CH:20]=1.CN([CH:24]=[O:25])C>CCOCC>[Cl:14][C:15]1[C:16]([CH:24]=[O:25])=[N:17][CH:18]=[CH:19][CH:20]=1

Komponenten

6

Edukt 4

HCID 6228DimethylformamideHCID 8037N,N,N',N'-TetramethylethylenediamineHCID 122873-ChloropyridineHCID 178418339Butyllithium

Produkt 1

HCID 107492803-Chloro-2-formylpyridineAusbeute 27 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 3283Diethyl EtherLösungsmittel2×

Versuchsvorschrift

To a solution of TMEDA (660 uL, 2.58 mmol) in ether (20 mL) at −78° C. was added a solution of n-butyl lithium in ether (2.5 M, 1.76 mL, 4.40 mmol). After 30 minutes at −78° C., 3-chloropyridine (419 uL, 4.40 mmol) was added. After another 2 hours at −78° C., DMF (375 uL, 4.84 mmol) was added. After a further 2 hours at −78° C., the reaction was quenched with saturated aqueous NaHCO3 (20 mL), extracted with ether (4×15 mL), dried (Na2SO4), filtered and concentrated in vacuo to give the crude oil. Purification by column chromatography on silica gel (Hexanes: EtOAc 4:1) afforded the title compound as a crystalline solid (168 mg, 27%). 1H NMR (CDCl3) 7.45 (dd, 1H, J=8.3, 4.4 Hz), 7.83 (dd, 1H, J=4.8, 1.4 Hz), 8.70 (dd, 1H, J=4.8, 1.5 Hz), 10.28 (s, 1H).

Aufarbeitung

  1. waitAfter another 2 hours at −78° C.
  2. waitAfter a further 2 hours at −78° C.
  3. customthe reaction was quenched with saturated aqueous NaHCO3 (20 mL)
  4. extractionextracted with ether (4×15 mL)
  5. dry with materialdried (Na2SO4)
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customto give the crude oil
  9. customPurification by column chromatography on silica gel (Hexanes: EtOAc 4:1)

Quellen und Nachweise

ORD-Eintrag
ord-3693043f7ce14a37a932a4eb4f180ad8
Quelldatensatz
uspto-grants-2006_08
Patentnummer
US07084155B2

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