2-Methyl-5-phenylpyridine → 5-Phenylpyridine-2-carbaldehyde

HRID 250949

Reaktionsgleichung

Reaktionsgleichung von HRID 250949
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)=[CH:4][N:3]=1.[O:14]1CCOCC1.O>>[C:8]1([C:5]2[CH:6]=[CH:7][C:2]([CH:1]=[O:14])=[N:3][CH:4]=2)[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1

Komponenten

3

Edukt 2

HCID 767442-Methyl-5-phenylpyridineHCID 218864351,4-Dioxane--water (1/1)

Produkt 1

HCID 263436035-Phenylpyridine-2-carbaldehydeAusbeute 14 %

Reaktionsbedingungen

Temperatur
110 °C

Versuchsvorschrift

To a solution of 2-methyl-5-phenyl-pyridine (800 mg, 4.73 mmol) (Koyama, J. et al. Heterocycles, 1994, 38, 1595-1600) in mixture of dioxane/water (20 mL:2 mL) was added SeO2 (577 mg, 5.20 mmol). The reaction mixture was heated to 110° C. overnight. Then the reaction mixture was cooled and concentrated in vacuo. Purification by flash column chromatography on silica gel using 1:4 hexanes/EtOAc afforded 5-phenyl-pyridine-2-carbaldehyde as a pale yellow solid (124 mg, 14%). 1H NMR (CDCl3) δ 7.49-7.52 (m, 3H), 7.63-7.66 (m, 2H), 8.05 (s, 2H), 9.02 (d, 1H, J=3.0 Hz), 10.12 (s, 1H).

Aufarbeitung

  1. temperatureThen the reaction mixture was cooled
  2. concentrationconcentrated in vacuo
  3. customPurification by flash column chromatography on silica gel using 1:4 hexanes/EtOAc

Quellen und Nachweise

ORD-Eintrag
ord-e5b04125e21845cbb205207d5bb7ac30
Quelldatensatz
uspto-grants-2011_01
Patentnummer
US07863293B2

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