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

HRID 31593

反応式

HRID 31593 の反応式
[CH3:1][O:2][CH:3]1[O:8][CH2:7][CH:6]([CH2:9][OH:10])[CH2:5][O:4]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][O:2][CH:3]1[O:8][CH2:7][CH:6]([CH2:9][O:10][C:14]2[CH:19]=[CH:18][N+:17]([O-:20])=[C:16]([CH3:21])[C:15]=2[CH3:22])[CH2:5][O:4]1

参加物

5

反応物 3

HCID 24758Sodium hydrideHCID 98774464-Chloro-2,3-dimethyl-1-oxidopyridin-1-iumHCID 59792360(2-Methoxy-1,3-dioxan-5-yl)methanol

生成物 1

HCID 597925894-((2-Methoxy-1,3-dioxan-5-yl)methoxy)-2,3-dimethylpyridine 1-oxide収率 49.5%

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-methoxy-1,3-dioxan-5-yl)methanol (2.0 g, 13.5 mmol) obtained in the same manner of step (6a), sodium hydride, in oil (770 mg, 14.9 mmol as the content was regarded as 55%) was added at room temperature. To the mixture, 4-chloro-2,3-dimethylpyridine 1-oxide (2.13 g, 13.5 mmol) was added and the mixture was stirred at 60° C. for 2.5 hours. After the reaction mixture was cooled to room temperature, it was concentrated. The residue was purified by silica gel column chromatography (NH silica gel, elution solvent: ethyl acetate/methanol) to obtain the title compound (1.8 g, 49.5% yield), which was a cis and trans (1:1) mixture, 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
  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-8999a2a805a14ab1ac0958124306d33d
出典データセット
uspto-grants-2008_09
特許番号
US07425634B2

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