Potassium Carbonate → 4-Methoxy-5-methyl-2-vinyl-pyridine

HRID 1908812Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1908812
Cl[C:2]1[CH:7]=[C:6]([O:8][CH3:9])[C:5]([CH3:10])=[CH:4][N:3]=1.B1(C=C)OB([CH:17]=[CH2:18])OB(C=C)O1.C1C=CN=CC=1.C([O-])([O-])=O.[K+].[K+]>COCCOC.O.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>[CH3:9][O:8][C:6]1[C:5]([CH3:10])=[CH:4][N:3]=[C:2]([CH:17]=[CH2:18])[CH:7]=1

Komponenten

7

Edukt 3

HCID 11430Potassium CarbonateHCID 27348062,4,6-Trivinylboroxin-Pyridine ComplexHCID 790022772-Chloro-4-methoxy-5-methylpyridine

Produkt 1

HCID 670271894-Methoxy-5-methyl-2-vinyl-pyridineAusbeute 62,9 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 178418397HCID 178418397, VerbindungKatalysatorHCID 962WaterLösungsmittelHCID 80711,2-DimethoxyethaneLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

To a solution of 2-chloro-4-methoxy-5-methyl-pyridine (2.91 g, 18.5 mmol) in DME (75 mL), 2,4,6-trivinylcyclotriboroxane pyridine complex (3.13 g, 13.0 mmol) followed by 2 M aq. K2CO3 solution (25 mL) is added. The mixture is degassed and put under argon before Pd(PPh3)4 (384 mg, 0.332 mmol) is added. The mixture is stirred at 80° C. for 15 h before it is cooled to rt, diluted with water and extracted with diethyl ether. The org. extract is washed with sat. aq. NaHCO3 solution, dried over MgSO4, filtered and concentrated. The crude product is purified by CC on silica gel eluting with heptane:EA 4:1 to give 4-methoxy-5-methyl-2-vinyl-pyridine (1.22 g) as a white solid; LC-MS: tR=0.52 min, [M+1]+=150.08.

Aufarbeitung

  1. additionis added
  2. customThe mixture is degassed
  3. additionis added
  4. temperatureis cooled to rt
  5. extractionextracted with diethyl ether
  6. extractionextract
  7. washis washed with sat. aq. NaHCO3 solution
  8. dry with materialdried over MgSO4
  9. filtrationfiltered
  10. concentrationconcentrated
  11. customThe crude product is purified by CC on silica gel eluting with heptane:EA 4:1

Quellen und Nachweise

ORD-Eintrag
ord-ca2ada2e64134ac2912c9f7c0ff006f3
Quelldatensatz
uspto-grants-2013_12
Patentnummer
US08598208B2

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