Sodium hydride → 4-((5,5-Dimethyl-1,3-dioxan-2-yl)methoxy)-2,3-dimethylpyridine 1-oxide

HRID 1645503Notes

Reaction equation

HRID 1645503 reaction equation
[CH3:1][C:2]1([CH3:10])[CH2:7][O:6][CH:5]([CH2:8][OH:9])[O:4][CH2:3]1.[H-].[Na+].Cl[C:14]1[CH:19]=[CH:18][N+:17]([O-:20])=[C:16]([CH3:21])[C:15]=1[CH3:22]>CS(C)=O>[CH3:1][C:2]1([CH3:10])[CH2:7][O:6][CH:5]([CH2:8][O:9][C:14]2[CH:19]=[CH:18][N+:17]([O-:20])=[C:16]([CH3:21])[C:15]=2[CH3:22])[O:4][CH2:3]1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 98774464-Chloro-2,3-dimethyl-1-oxidopyridin-1-iumHCID 59792511(5,5-Dimethyl-1,3-dioxan-2-yl)methanol

Product 1

HCID 597925544-((5,5-Dimethyl-1,3-dioxan-2-yl)methoxy)-2,3-dimethylpyridine 1-oxideYield 84.6%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

The (5,5-dimethyl-1,3-dioxan-2-yl)methanol (2 g, 13.7 mmol) obtained in the step (1b) was mixed with sodium hydride in oil (822 mg, 20.6 mmol as the content was regarded as 60%) and dimethylsulfoxide (20 ml). The mixture was stirred at room temperature for 30 minutes. To the reaction mixture, 4-chloro-2,3-dimethylpyridine 1-oxide (2.16 g, 13.7 mmol) was added and stirred at 50° C. overnight, and further allowed to stand still for one day at room temperature. After dimethylsulfoxide was distilled off, methanol and NH silica gel were added to the residue and then methanol was distilled off. The mixture of the reaction mixture and NH silica gel was purified by silica gel column chromatography (NH silica gel: 200 g, elution solvent: ethyl acetate/heptane=1/1 to 4/1→methanol/ethyl acetate=1/9) to obtain the title compound (3.1 g, yield: 84.6%) as a light yellow oil.

Workup

  1. stirringstirred at 50° C. overnight
  2. waitto stand still for one day at room temperature
  3. distillationAfter dimethylsulfoxide was distilled off
  4. additionmethanol and NH silica gel were added to the residue
  5. distillationmethanol was distilled off
  6. additionThe mixture of the reaction mixture and NH silica gel
  7. customwas purified by silica gel column chromatography (NH silica gel: 200 g, elution solvent: ethyl acetate/heptane=1/1 to 4/1→methanol/ethyl acetate=1/9)

Sources & evidence

ORD record
ord-fc05749c133f48a494e8f213d30aed57
Source dataset
uspto-grants-2012_02
Patent number
US08124780B2

Reaction notes

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