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

HRID 850603Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 850603
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 7-2 (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 is heated at 90° C. for 12 hr, then the volatiles were removed m 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 7-3 as a yellow solid. 1H NMR (300 MHz, CDCl3) δ 1.34 (3H, t), 3.97 (3H, s), 4.26 (2H, q), 6.34 (1H, d),6.76 (1H, d), 7.63 (1H, d), 7.77 (1H, dd),8.27 (1H, d).

Aufarbeitung

  1. customthe volatiles were removed m 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-1a26600da96f4bd195aa6091e29fdbf8
Quelldatensatz
uspto-grants-2000_01
Patentnummer
US06017926

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