Sodium hydride → 4-(((4R)-2,2-dimethyl-1,3-dioxolan-4-yl)methoxy)-2,3-dimethylpyridine 1-oxide

HRID 31620

反応式

HRID 31620 の反応式
[CH3:1][C:2]1([CH3:9])[O:6][C@H:5]([CH2:7][OH:8])[CH2:4][O:3]1.[H-].[Na+].Cl[C:13]1[CH:18]=[CH:17][N+:16]([O-:19])=[C:15]([CH3:20])[C:14]=1[CH3:21]>CS(C)=O>[CH3:1][C:2]1([CH3:9])[O:6][C@H:5]([CH2:7][O:8][C:13]2[CH:18]=[CH:17][N+:16]([O-:19])=[C:15]([CH3:20])[C:14]=2[CH3:21])[CH2:4][O:3]1

参加物

5

反応物 3

HCID 24758Sodium hydrideHCID 736056(R)-SolketalHCID 98774464-Chloro-2,3-dimethyl-1-oxidopyridin-1-ium

生成物 1

HCID 597925474-(((4R)-2,2-dimethyl-1,3-dioxolan-4-yl)methoxy)-2,3-dimethylpyridine 1-oxide収率 136%

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 (48 ml) solution of the ((4R)-2,2-dimethyl-1,3-dioxolan-4-yl)methanol (4.87 g, 39.7 mmol), sodium hydride, in oil (1.73 g, 39.6 mmol as the content was regarded as 55%) was added at room temperature. To the mixture, 4-chloro-2,3-dimethylpyridine 1-oxide (4.8 g, 30.5 mmol) was added, the mixture was stirred at 60° C. for 2 hours. After cooled to room temperature, the reaction mixture was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (NH silica gel, elution solvent: ethyl acetate/methanol) to obtain the title compound (10.5 g, yield: 136%) as a yellow oil.

後処理

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

出典と根拠

ORDレコード
ord-de375aaca8f74071bd9828ec77c4050a
出典データセット
uspto-grants-2008_09
特許番号
US07425634B2

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