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

HRID 31593

반응식

HRID 31593 반응식
[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

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 679Dimethyl Sulfoxide용매

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온도
60 °C

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-8999a2a805a14ab1ac0958124306d33d
출처 데이터셋
uspto-grants-2008_09
특허 번호
US07425634B2

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