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

HRID 31597

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HRID 31597 반응식
[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

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 679Dimethyl Sulfoxide용매

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온도
60 °C

실험 절차

To a dimethylsulfoxide (10 ml) solution of the (2,2-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.

후처리

  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)

출처 및 근거

ORD 기록
ord-9212ce16c1ab41cd8b73cacabfbfdd81
출처 데이터셋
uspto-grants-2008_09
특허 번호
US07425634B2

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