Sulfuric Acid → 2-(3-Methyl-4-chloro-pyridin-2-yl)-2-cyclopropyl-acetaldehyde

HRID 1478295Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1478295
[CH:1]1([C:4]([C:8]2[C:13]([CH3:14])=[C:12]([Cl:15])[CH:11]=[CH:10][N:9]=2)=[CH:5][O:6]C)[CH2:3][CH2:2]1.S(=O)(=O)(O)O.[OH-].[Na+]>C(O)(=O)C>[CH3:14][C:13]1[C:8]([CH:4]([CH:1]2[CH2:3][CH2:2]2)[CH:5]=[O:6])=[N:9][CH:10]=[CH:11][C:12]=1[Cl:15]

Komponenten

5

Edukt 3

HCID 1118Sulfuric AcidHCID 14798Sodium HydroxideHCID 669802244-Chloro-2-(1-cyclopropyl-2-methoxyvinyl)-3-methylpyridine

Produkt 1

HCID 186293552-(3-Methyl-4-chloro-pyridin-2-yl)-2-cyclopropyl-acetaldehydeAusbeute 80,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 176Acetic AcidLösungsmittel

Versuchsvorschrift

A solution of 2-(1-cyclopropyl-2-methoxy-vinyl)-3-methyl-4-chloro-pyridine (6.41 g, 28.7 mmol) in acetic acid (50 mL) was treated with sulfuric acid (6.52 mL, 143 mmol) at room temperature overnight. The reaction mixture was neutralized with 2N NaOH to pH 8-9 extracted with ethyl acetate (2×100 mL). The organic phases were combined, dried, and concentrated. The residue was purified by flash silica column chromatography (hexane/ethyl acetate=2:1) to afford the title compound as a yellow solid (4.83 g, 80%).

Aufarbeitung

  1. extractionextracted with ethyl acetate (2×100 mL)
  2. customdried
  3. concentrationconcentrated
  4. customThe residue was purified by flash silica column chromatography (hexane/ethyl acetate=2:1)

Quellen und Nachweise

ORD-Eintrag
ord-dad976c4da9b4722ae59cd4a96833f13
Quelldatensatz
uspto-grants-2016_08
Patentnummer
US09403818B2

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