Ethanol → 4-(4-Methoxypyrimidin-2-YL)benzaldehyde

HRID 1166089Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1166089
C([O-])([O-])=O.[Na+].[Na+].C(O)C.Cl[C:11]1[N:16]=[C:15]([O:17][CH3:18])[CH:14]=[CH:13][N:12]=1.[CH:19]([C:21]1[CH:26]=[CH:25][C:24](B(O)O)=[CH:23][CH:22]=1)=[O:20]>C1(C)C=CC=CC=1.C(OCC)(=O)C.C1C=CC(P(C2C=CC=CC=2)CCCCP(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.Cl[Pd]Cl>[CH3:18][O:17][C:15]1[CH:14]=[CH:13][N:12]=[C:11]([C:24]2[CH:25]=[CH:26][C:21]([CH:19]=[O:20])=[CH:22][CH:23]=2)[N:16]=1

Komponenten

8

Edukt 4

HCID 702EthanolHCID 10340Sodium CarbonateHCID 5889352-Chloro-4-methoxypyrimidineHCID 5910734-Formylphenylboronic Acid

Produkt 1

HCID 226310554-(4-Methoxypyrimidin-2-YL)benzaldehydeAusbeute 42 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 10974057(Butane-1,4-diyl)bis(diphenylphosphane)--dichloropalladium (1/1)KatalysatorHCID 1140TolueneLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

1 M aq. Na2CO3 (20 mL) and ethanol (10 mL) were added to a solution of 2-chloro-4-methoxypyrimidine (2.90 g, 20.06 mmol, prepared as described in Tetrahedron 1997, 53, 11595), 4-formylphenylboronic acid (3.90 g, 26.01 mmol) and [1,4-bis(diphenylphosphino)butane]palladium(II) dichloride (0.60 g, 0.99 mmol) in toluene (40 mL) and the mixture was heated to reflux for 18 h. The cooled reaction mixture was diluted with ethyl acetate, washed with sat. aq. NaHCO3 and brine, dried (MgSO4), and concentrated. Purification by chromatography (SiO2, 4:1 hexane/ethyl acetate) yielded 1.80 g (42%) of the title compound. MS 215 (M+H)+.

Aufarbeitung

  1. temperaturethe mixture was heated
  2. temperatureto reflux for 18 h
  3. customThe cooled reaction mixture
  4. washwashed with sat. aq. NaHCO3 and brine
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated
  7. customPurification by chromatography (SiO2, 4:1 hexane/ethyl acetate)

Quellen und Nachweise

ORD-Eintrag
ord-c7839aee1f174c92b543e0ab98f05371
Quelldatensatz
uspto-grants-2003_09
Patentnummer
US06613747B2

Notizen zur Reaktion

Wird geladen…