4-(4-Methoxy-2,6-dimethyl-phenyl)-3,5-dimethyl-pyridin-1-ol → 4-(4-Methoxy-2,6-dimethyl-phenyl)-3,5-dimethyl-pyridine

HRID 1169524Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1169524
[CH3:1][O:2][C:3]1[CH:8]=[C:7]([CH3:9])[C:6]([C:10]2[C:15]([CH3:16])=[CH:14][N:13](O)[CH2:12][C:11]=2[CH3:18])=[C:5]([CH3:19])[CH:4]=1.O.[PH2]([O-])=O.[Na+]>C(O)(=O)C.[Pd]>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH3:19])[C:6]([C:10]2[C:15]([CH3:16])=[CH:14][N:13]=[CH:12][C:11]=2[CH3:18])=[C:7]([CH3:9])[CH:8]=1

Komponenten

5

Edukt 2

HCID 669931454-(4-Methoxy-2,6-dimethyl-phenyl)-3,5-dimethyl-pyridin-1-olHCID 178418950HCID 178418950, Verbindung

Produkt 1

HCID 595503344-(4-Methoxy-2,6-dimethyl-phenyl)-3,5-dimethyl-pyridineAusbeute 97,9 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23938PalladiumKatalysatorHCID 176Acetic AcidLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

To a mixture of 3 (6.55 g, 25.5 mmol) and palladium (10 wt. % on activated carbon; 3.05 g, 2.8 mmol) in acetic acid (150 mL) was added sodium hypophosphite hydrate (6.7 g, 63 mmol) in a single portion at 80° C. The reaction mixture was stirred at 80° C. under N2 for 12 h, then filtered and concentrated in vacuo. The resulting light-yellow oil was dissolved in chloroform (250 mL) and washed successively with saturated NaHCO3 (aq.), water, and brine. The organic layer was then separated, dried over MgSO4, filtered, and concentrated in vacuo. The resulting pale-yellow solid was purified by flash chromatography on silica gel eluting with 1:1 hexane: ethyl acetate, to give 6.01 g (97.9%) of the title compound as colorless solid: mp 87-88° C.; 1H NMR (400 MHz, CD2Cl2): δ 8.334 (s, 2H), 6.707 (s, 2H), 3.804 (s, 3H), 1.892 (s, 6H), 1.851 (s, 6H); 13C NMR (100 MHz, CD2Cl2): δ 159.330, 148.939, 148.420, 136.373, 131.905, 129.958, 113.489, 55.556, 20.188, 16.831; MS (APCI): m/z 242.2 [(M+H)+, 100]; Anal. Calcd. For C16H19NO: C, 79.63; H, 7.94; N, 5.80. Found: C, 79.39; H, 7.94; N, 5.75.

Aufarbeitung

  1. filtrationfiltered
  2. concentrationconcentrated in vacuo
  3. dissolutionThe resulting light-yellow oil was dissolved in chloroform (250 mL)
  4. washwashed successively with saturated NaHCO3 (aq.), water, and brine
  5. customThe organic layer was then separated
  6. dry with materialdried over MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo
  9. customThe resulting pale-yellow solid was purified by flash chromatography on silica gel eluting with 1:1 hexane

Quellen und Nachweise

ORD-Eintrag
ord-d29732126d7b4c81a0b348d1e2a22805
Quelldatensatz
uspto-grants-2010_11
Patentnummer
US07824582B2

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