Sodium hydride → 2,3-Dimethyl-4-((1-methyl-2,6,7-trioxabicyclo[2.2.2]oct-4-yl)methoxy)pyridine 1-oxide

HRID 31632Notes

Reaction equation

[CH3:1][C:2]12[O:9][CH2:8][C:5]([CH2:10][OH:11])([CH2:6][O:7]1)[CH2:4][O:3]2.[H-].[Na+].Cl[C:15]1[CH:20]=[CH:19][N+:18]([O-:21])=[C:17]([CH3:22])[C:16]=1[CH3:23]>CS(C)=O>[CH3:22][C:17]1[C:16]([CH3:23])=[C:15]([O:11][CH2:10][C:5]23[CH2:4][O:3][C:2]([CH3:1])([O:7][CH2:6]2)[O:9][CH2:8]3)[CH:20]=[CH:19][N+:18]=1[O-:21]

Participants

Conditions

Temperature: 60 °C

Procedure

To a dimethylsulfoxide solution (30 ml) of the (1-methyl-2,6,7-trioxabicyclo[2.2.2]oct-4-yl)methanol (4.5 g, 28.1 mmol) obtained in the step (24a), sodium hydride, in oil (1.29 g, 29.5 mmol as the content was regarded as 55%) was added at room temperature. To the mixture, 4-chloro-2,3-dimethylpyridine 1-oxide (3.99 g, 25.3 mmol) was added, which was stirred at 60° C. for 3 hours. After cooled to room temperature, the reaction mixture was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (elution solvent: ethyl acetate/methanol) to obtain the title compound (7.46 g, yield: 81%) as a yellow oil.

Workup

additionwas added at room temperature
temperatureAfter cooled to room temperature
concentrationthe reaction mixture was concentrated under reduced pressure
customThe residue was purified by silica gel column chromatography (elution solvent: ethyl acetate/methanol)

Sources & evidence

ORD record: ord-a704b61e2aac494dbb30410dc92615cc
Source dataset: uspto-grants-2008_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07425634B2

Reaction notes

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