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

HRID 1645536Notes

Reaction equation

[F:1][CH2:2][C:3]1([CH2:11][F:12])[O:8][CH2:7][CH:6]([CH2:9][OH:10])[CH2:5][O:4]1.[H-].[Na+].Cl[C:16]1[CH:21]=[CH:20][N+:19]([O-:22])=[C:18]([CH3:23])[C:17]=1[CH3:24]>CS(C)=O>[F:1][CH2:2][C:3]1([CH2:11][F:12])[O:4][CH2:5][CH:6]([CH2:9][O:10][C:16]2[CH:21]=[CH:20][N+:19]([O-:22])=[C:18]([CH3:23])[C:17]=2[CH3:24])[CH2:7][O:8]1

Participants

Conditions

Temperature: 60 °C

Procedure

To a dimethylsulfoxide (10 ml) solution of the (2,2-bis(fluoromethyl)-1,3-dioxan-5-yl)methanol (1.6 g, 8.98 mmol) obtained in the step (7a), sodium hydride, in oil (431 mg, 9.88 mmol as the content was regarded as 55%) was added at room temperature. To the mixture, 4-chloro-2,3-dimethylpyridine 1-oxide (1.42 g, 8.98 mmol) was added and the mixture was stirred at 60° C. for 2 hours. After the reaction mixture was cooled to room temperature, it was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (elution solvent: ethyl acetate/methanol) to obtain the title compound (1.63 g, yield: 60.6%) as a yellow oil.

Workup

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

Sources & evidence

ORD record: ord-217466cc98404d0b86a7bacce3051399
Source dataset: uspto-grants-2012_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08124780B2

Reaction notes

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