Benzene → 2-Methyl-3-(2-phenyl-2-propanyl)pyridine

HRID 1592419Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1592419
[Al+3].[Cl-].[Cl-].[Cl-].[CH3:5][C:6]1[C:11]([C:12](O)([CH3:14])[CH3:13])=[CH:10][CH:9]=[CH:8][N:7]=1.[OH-].[Na+].[CH:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1>CCOC(C)=O>[CH3:5][C:6]1[C:11]([C:12]([CH3:14])([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[CH3:13])=[CH:10][CH:9]=[CH:8][N:7]=1

Komponenten

6

Edukt 4

HCID 241Benzene2×HCID 14798Sodium HydroxideHCID 6451240Aluminum(III) ChlorideHCID 450917322-(2-Methylpyridin-3-yl)propan-2-ol

Produkt 1

HCID 450972722-Methyl-3-(2-phenyl-2-propanyl)pyridineAusbeute 75 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

To a mixture of AlCl3 (2.173 g, 16.3 mmol) in benzene (20 mL) was added a solution of 2-(2-methyl-pyridin-3-yl)-propan-2-ol (0.455 g, 3.00 mmol) in benzene (10 mL) and the resultant mixture was stirred at room temperature overnight. The mixture was poured onto ice (200 mL), diluted with EtOAc (200 mL), and neutralized with 10 N NaOH (4 mL). The phases were separated and the organic phase was washed with brine (3×25 mL), dried (MgSO4), and concentrated. Purification of the crude material by column chromatography on silica gel (20:1 CH2Cl2-MeOH) provided 0.479 g (75%) of 2-methyl-3-(1-methyl-1-phenyl-ethyl)-pyridine as a colorless oil. 1H NMR (CDCl3) δ 1.68 (s, 6H), 2.01 (s, 3H), 7.11-7.20 (m, 4H), 7.24-7.30 (m, 2H), 7.86 (dd, 1H, J=8.1, 1.5 Hz), 8.39 (dd, 1H, J=4.8, 1.5 Hz).

Aufarbeitung

  1. additionThe mixture was poured onto ice (200 mL)
  2. customThe phases were separated
  3. washthe organic phase was washed with brine (3×25 mL)
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated
  6. customPurification of the crude material by column chromatography on silica gel (20:1 CH2Cl2-MeOH)

Quellen und Nachweise

ORD-Eintrag
ord-bfc70b1d4ee64e9bbf1c03e1717c6429
Quelldatensatz
uspto-grants-2007_11
Patentnummer
US07291631B2

Notizen zur Reaktion

Wird geladen…