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

HRID 31597

反応式

HRID 31597 の反応式
[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

参加物

5

反応物 3

HCID 24758Sodium hydrideHCID 98774464-Chloro-2,3-dimethyl-1-oxidopyridin-1-iumHCID 59792580(2,2-Bis(fluoromethyl)-1,3-dioxan-5-yl)methanol

生成物 1

HCID 597924924-((2,2-Bis(fluoromethyl)-1,3-dioxan-5-yl)methoxy)-2,3-dimethylpyridine 1-oxide収率 60.6%

試薬・触媒・溶媒 1

HCID 679Dimethyl Sulfoxide溶媒

反応条件

温度
60 °C

実験手順

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.

後処理

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

出典と根拠

ORDレコード
ord-9212ce16c1ab41cd8b73cacabfbfdd81
出典データセット
uspto-grants-2008_09
特許番号
US07425634B2

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