Allyl Alcohol → 6-Quinoxalinepropanal

HRID 500190Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 500190
Br[C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[CH:7][CH:6]=[N:5]2.[CH2:12]([OH:15])[CH:13]=[CH2:14].C1(N(C)C2CCCCC2)CCCCC1>O1CCOCC1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].F[B-](F)(F)F.C([PH+](C(C)(C)C)C(C)(C)C)(C)(C)C>[N:8]1[C:9]2[C:4](=[CH:3][C:2]([CH2:14][CH2:13][CH:12]=[O:15])=[CH:11][CH:10]=2)[N:5]=[CH:6][CH:7]=1

Komponenten

7

Edukt 3

HCID 7858Allyl AlcoholHCID 24210N-Methyl dicyclohexylamineHCID 6109396-Bromoquinoxaline

Produkt 1

HCID 866215076-QuinoxalinepropanalAusbeute 55,1 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 2734635Tri-tert-butylphosphine tetrafluoroborateKatalysatorHCID 9811564Bis(dibenzylideneacetone)palladiumKatalysatorHCID 312751,4-DioxaneLösungsmittel

Reaktionsbedingungen

Temperatur
40 °C

Versuchsvorschrift

A mixture of 6-bromoquinoxaline (0.40 g, 1.9 mmol), 2-propen-1-ol (0.260 mL, 3.8 mmol), tris(dibenzylideneacetone)dipalladium (26 mg, 0.029 mmol), tri-tert-butylphosphonium tetrafluoroborate (16 mg, 0.057 mmol) and N-cyclohexyl-N-methyl-cyclohexanamine (0.49 mL, 2.3 mmol) in 1,4-dioxane (3.0 mL) was stirred at 40° C. overnight. After cooling to RT, the mixture was filtered, washed with methylene chloride and the filtrate was concentrated. The crude material was purified by chromatography on silica gel with EtOAc in Hexane (0-40%) to afford the desired product (195 mg). LCMS: (M+H)=187.3.

Aufarbeitung

  1. temperatureAfter cooling to RT
  2. filtrationthe mixture was filtered
  3. washwashed with methylene chloride
  4. concentrationthe filtrate was concentrated
  5. customThe crude material was purified by chromatography on silica gel with EtOAc in Hexane (0-40%)

Quellen und Nachweise

ORD-Eintrag
ord-84d676333b37460fae98b3ab0234f95f
Quelldatensatz
uspto-grants-2010_08
Patentnummer
US07767675B2

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