Ethylenediaminetetraacetic Acid → 4-Methoxy-2-methylpyridine

HRID 273326

Reaktionsgleichung

Reaktionsgleichung von HRID 273326
[Cl-].C[Zn+].Cl[C:5]1[CH:10]=[C:9]([O:11][CH3:12])[CH:8]=[CH:7][N:6]=1.[CH2:13](N(CC(O)=O)CC(O)=O)CN(CC(O)=O)CC(O)=O.C([O-])([O-])=O.[K+].[K+]>C1COCC1.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH3:12][O:11][C:9]1[CH:8]=[CH:7][N:6]=[C:5]([CH3:13])[CH:10]=1

Komponenten

7

Edukt 4

HCID 6049Ethylenediaminetetraacetic AcidHCID 11430Potassium CarbonateHCID 19911282-Chloro-4-methoxypyridineHCID 178477797HCID 178477797, Verbindung

Produkt 1

HCID 47377584-Methoxy-2-methylpyridineAusbeute 50 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 178418397HCID 178418397, VerbindungKatalysatorHCID 8028TetrahydrofuranLösungsmittel2×

Versuchsvorschrift

Methylzinc chloride in THF (2 M, 10.489 mL, 21 mmol) was added to a solution of 2-chloro-4-methoxypyridine (0.500 g, 3.48 mmol) and Pd(PPh3)4 (0.161 g, 0.14 mmol) in THF (10 mL). The mixture was refluxed for 40 h and then poured into an aqueous solution (10 mL) containing ethylenediaminetetraacetic acid (1.5 g). The resulting mixture was neutralized with K2CO3 and extracted with Et2O. The organic layer was concentrated to give a residue, which was purified on a silica gel column eluting with MeOH:EtOAc (1:10) to give 4-methoxy-2-methylpyridine (0.213 g, 50.0%).

Aufarbeitung

  1. temperatureThe mixture was refluxed for 40 h
  2. extractionextracted with Et2O
  3. concentrationThe organic layer was concentrated
  4. customto give a residue, which
  5. customwas purified on a silica gel column
  6. washeluting with MeOH:EtOAc (1:10)

Quellen und Nachweise

ORD-Eintrag
ord-e810fdf5a0ca4f1d9c55403b4f5a9099
Quelldatensatz
uspto-grants-2008_11
Patentnummer
US07456289B2

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