Triethylamine → Ethyl 3-(6-methoxy-3-pyridyl)acrylate

HRID 379252Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 379252
Br[C:2]1[CH:3]=[CH:4][C:5]([O:8][CH3:9])=[N:6][CH:7]=1.[C:10]([O:14][CH2:15][CH3:16])(=[O:13])[CH:11]=[CH2:12].C(N(CC)CC)C.C1(C)C=CC=CC=1P(C1C=CC=CC=1C)C1C=CC=CC=1C>C(#N)C.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[CH3:9][O:8][C:5]1[N:6]=[CH:7][C:2]([CH:12]=[CH:11][C:10]([O:14][CH2:15][CH3:16])=[O:13])=[CH:3][CH:4]=1

Komponenten

7

Edukt 4

HCID 8471TriethylamineHCID 8821Ethyl AcrylateHCID 80271Tri-o-tolylphosphineHCID 27348955-Bromo-2-methoxypyridine

Produkt 1

HCID 53930754Ethyl 3-(6-methoxy-3-pyridyl)acrylate

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 167845palladium(II) acetateKatalysatorHCID 6342AcetonitrileLösungsmittel

Reaktionsbedingungen

Temperatur
90 °C

Versuchsvorschrift

A solution of the 5-bromo-2-methoxypyridine 16-2 (74.3 g, 0.4 mol), ethyl acrylate (150 mL, 1.4 mol), triethylamine (150 mL, 1.08 mol), palladium acetate (10 g, 0.045 mol) and tri-o-tolylphosphine (20 g, 0.066 mol) in 100 mL acetonitrile was degassed with argon for 10 minutes. The mixture was heated at 90° C. for 12 hr, then the volatiles were removed in vacuo. Toluene (300 mL) was added and the mixture concentrated again. Diethyl ether (300 mL) was added and the mixture filtered through a pad of silica gel eluting with 800 mL of diethyl ether. After removal of the diethyl ether, the residue was chromatographed on silica gel eluting with EtOAc/hexane, 1:19 then 1:14 then 1:9 to give 16-3 as a yellow solid.

Aufarbeitung

  1. customthe volatiles were removed in vacuo
  2. additionToluene (300 mL) was added
  3. concentrationthe mixture concentrated again
  4. additionDiethyl ether (300 mL) was added
  5. filtrationthe mixture filtered through a pad of silica gel eluting with 800 mL of diethyl ether
  6. customAfter removal of the diethyl ether
  7. customthe residue was chromatographed on silica gel eluting with EtOAc/hexane, 1:19

Quellen und Nachweise

ORD-Eintrag
ord-d62bc6c0881343ef8e9df67de26e597e
Quelldatensatz
uspto-grants-2001_10
Patentnummer
US06297249B1

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