4-((2,2-Dimethyl-1,3-dioxan-5-yl)methoxy)-2,3,5-trimethylpyridine 1-oxide → HCID 59792553, compound

HRID 1645679Notes

Reaction equation

HRID 1645679 reaction equation
[CH3:1][C:2]1([CH3:20])[O:7][CH2:6][CH:5]([CH2:8][O:9][C:10]2[C:15]([CH3:16])=[CH:14][N+:13]([O-])=[C:12]([CH3:18])[C:11]=2[CH3:19])[CH2:4][O:3]1>C(OC(=O)C)(=O)C>[C:2]([O:7][CH2:18][C:12]1[C:11]([CH3:19])=[C:10]([O:9][CH2:8][CH:5]2[CH2:6][O:7][C:2]([CH3:20])([CH3:1])[O:3][CH2:4]2)[C:15]([CH3:16])=[CH:14][N:13]=1)(=[O:3])[CH3:1]

Participants

3

Reactant 1

HCID 248160494-((2,2-Dimethyl-1,3-dioxan-5-yl)methoxy)-2,3,5-trimethylpyridine 1-oxide

Product 1

HCID 59792553HCID 59792553, compoundYield 100.9%

Reagents, catalysts & solvents 1

HCID 7918Acetic AnhydrideSolvent

Conditions

Temperature
85 °C

Procedure

4-((2,2-dimethyl-1,3-dioxan-5-yl)methoxy)-2,3,5-trimethylpyridine 1-oxide (10.5 g, 37.4 mmol) was dissolved in acetic anhydride (100 mL) and the solution was stirred at 85° C. for 1.5 hours. After the reaction mixture was concentrated, the residue was purified by silica gel column chromatography (elution solvent: n-heptane/ethyl acetate=1/1→0/1) and a desired fraction was concentrated to obtain the title compound (6.1 g, 50.4%) as a light yellow solid.

Workup

  1. concentrationAfter the reaction mixture was concentrated
  2. customthe residue was purified by silica gel column chromatography (elution solvent: n-heptane/ethyl acetate=1/1→0/1)
  3. concentrationa desired fraction was concentrated

Sources & evidence

ORD record
ord-1b7520794476472185dadf7e2ef9c9b9
Source dataset
uspto-grants-2012_02
Patent number
US08124780B2

Reaction notes

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