2,3-Dimethyl-4-(2-(2-propyl-1,3-dioxolan-2-yl)ethoxy)pyridine 1-oxide → (3-Methyl-4-(2-(2-propyl-1,3-dioxolan-2-yl)ethoxy)pyridin-2-yl)methyl acetate

HRID 1645515Notes

Reaction equation

[CH3:1][C:2]1[C:7]([CH3:8])=[C:6]([O:9][CH2:10][CH2:11][C:12]2([CH2:17][CH2:18][CH3:19])[O:16][CH2:15][CH2:14][O:13]2)[CH:5]=[CH:4][N+:3]=1[O-]>C(OC(=O)C)(=O)C>[C:12]([O:16][CH2:1][C:2]1[C:7]([CH3:8])=[C:6]([O:9][CH2:10][CH2:11][C:12]2([CH2:17][CH2:18][CH3:19])[O:16][CH2:15][CH2:14][O:13]2)[CH:5]=[CH:4][N:3]=1)(=[O:13])[CH3:11]

Participants

Conditions

Temperature: 80 °C

Procedure

The 2,3-dimethyl-4-(2-(2-propyl-1,3-dioxolan-2-yl)ethoxy)pyridine 1-oxide (1.53 g, 5.44 mmol) obtained in the step (3c) was mixed with acetic anhydride (30 ml) and the mixture was stirred at 80° C. overnight. The reaction mixture was concentrated under reduced pressure and the residue was dissolved in ethyl acetate and then subjected to silica gel column chromatography (elution solvent: n-heptane/ethyl acetate=1/1) to obtain the title compound (1.19 g, 67.6%) as a light yellow oil.

Workup

concentrationThe reaction mixture was concentrated under reduced pressure
dissolutionthe residue was dissolved in ethyl acetate
washsubjected to silica gel column chromatography (elution solvent: n-heptane/ethyl acetate=1/1)

Sources & evidence

ORD record: ord-17916fc605824a4eb18edefed61b7ea8
Source dataset: uspto-grants-2012_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08124780B2

Reaction notes

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