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

HRID 31620

반응식

HRID 31620 반응식
[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

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 679Dimethyl Sulfoxide용매

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온도
60 °C

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-de375aaca8f74071bd9828ec77c4050a
출처 데이터셋
uspto-grants-2008_09
특허 번호
US07425634B2

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