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

HRID 1478295Notes

Reaction equation

HRID 1478295 reaction equation
[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]

Participants

5

Reactant 3

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

Product 1

HCID 186293552-(3-Methyl-4-chloro-pyridin-2-yl)-2-cyclopropyl-acetaldehydeYield 80.3%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

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%).

Workup

  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)

Sources & evidence

ORD record
ord-dad976c4da9b4722ae59cd4a96833f13
Source dataset
uspto-grants-2016_08
Patent number
US09403818B2

Reaction notes

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