Water → (Z)-ethyl 3-(2-methylquinolin-8-yl)but-2-enoate

HRID 339037

Reaktionsgleichung

Reaktionsgleichung von HRID 339037
Br[C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:11]=1[N:10]=[C:9]([CH3:12])[CH:8]=[CH:7]2.[C:13]([O:18][CH2:19][CH3:20])(=[O:17])/[CH:14]=[CH:15]/[CH3:16].C1(N(C)C2CCCCC2)CCCCC1.O>O1CCOCC1.CC(C)([P](C(C)(C)C)([Pd][P](C(C)(C)C)(C(C)(C)C)C(C)(C)C)C(C)(C)C)C.C(OCC)(=O)C>[CH3:12][C:9]1[CH:8]=[CH:7][C:6]2[C:11](=[C:2](/[C:15](/[CH3:16])=[CH:14]\[C:13]([O:18][CH2:19][CH3:20])=[O:17])[CH:3]=[CH:4][CH:5]=2)[N:10]=1

Komponenten

8

Edukt 4

HCID 962WaterHCID 24210N-Methyl dicyclohexylamineHCID 429065Ethyl trans-crotonateHCID 47150308-Bromo-2-methylquinoline

Produkt 1

HCID 70983529(Z)-ethyl 3-(2-methylquinolin-8-yl)but-2-enoateAusbeute 35,2 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 178418851HCID 178418851, VerbindungKatalysatorHCID 8857Ethyl AcetateLösungsmittelHCID 312751,4-DioxaneLösungsmittel

Versuchsvorschrift

A solution of 8-bromo-2-methylquinoline (2.00 g, 9.01 mmol), (E)-ethyl but-2-enoate (3.36 mL, 27.0 mmol), N-cyclohexyl-N-methylcyclohexanamine (5.79 mL, 27.0 mmol), and Pd(PtBu3)2 (0.23 g, 0.45 mmol) in dioxane (10 mL) was stirred at reflux for 20 hours. After cooling to ambient temperature, water (20 mL) and ethyl acetate (30 mL) were added. The organic layer was separated, washed with brine, dried (sodium sulfate), filtered and concentrated under reduced pressure. The residue was purified by C-18 reverse phase flash chromatography (Biotage SP4 unit, C-18 40M column, 0-100% CH3CN/water gradient; 30 column volumes) to give (Z)-ethyl 3-(2-methylquinolin-8-yl)but-2-enoate (0.81 g, 35.2%) as a solid.

Aufarbeitung

  1. temperatureat reflux for 20 hours
  2. customThe organic layer was separated
  3. washwashed with brine
  4. dry with materialdried (sodium sulfate)
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by C-18 reverse phase flash chromatography (Biotage SP4 unit

Quellen und Nachweise

ORD-Eintrag
ord-95ffce153e0a46418ceb309f184b570f
Quelldatensatz
uspto-grants-2014_11
Patentnummer
US08889704B2

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