Sodium hydride → 4-(5,7-Dioxaspiro[2.5]oct-6-ylmethoxy)-2,3-dimethylpyridine 1-oxide

HRID 31571

반응식

HRID 31571 반응식
[CH2:1]1[C:3]2([CH2:8][O:7][CH:6]([CH2:9][OH:10])[O:5][CH2:4]2)[CH2:2]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>[CH2:2]1[C:3]2([CH2:8][O:7][CH:6]([CH2:9][O:10][C:14]3[CH:19]=[CH:18][N+:17]([O-:20])=[C:16]([CH3:21])[C:15]=3[CH3:22])[O:5][CH2:4]2)[CH2:1]1

참가 물질

5

반응물 3

HCID 24758Sodium hydrideHCID 98774464-Chloro-2,3-dimethyl-1-oxidopyridin-1-iumHCID 597925305,7-Dioxaspiro[2.5]oct-6-ylmethanol

생성물 1

HCID 597925884-(5,7-Dioxaspiro[2.5]oct-6-ylmethoxy)-2,3-dimethylpyridine 1-oxide수율 57.5%

시약·촉매·용매 1

HCID 679Dimethyl Sulfoxide용매

실험 절차

The 5,7-dioxaspiro[2.5]oct-6-ylmethanol (1.7 g, 11.8 mmol) obtained by the step (2b) was mixed with sodium hydride, in oil (708 mg, 17.7 mmol as the content was regarded as 60%) and dimethylsulfoxide (20 ml), and the mixture was stirred at room temperature for 30 minutes. To the reaction mixture, 4-chloro-2,3-dimethylpyridine1-oxide (1.86 g, 11.8 mmol) was added and stirred at 50° C. overnight. After dimethylsulfoxide was distilled off, methanol and NH silica gel were added to the residue and methanol was distilled off. The mixture of the reaction mixture and NH silica gel was purified by silica gel column chromatography (NH silica gel: 200 g, elution solvent: ethyl acetate/heptane=1/1 to 4/1→methanol/ethyl acetate=1/9 to 1/4) to obtain the title compound (1.8 g, yield: 57.5%) as a red oil.

후처리

  1. stirringstirred at 50° C. overnight
  2. distillationAfter dimethylsulfoxide was distilled off
  3. additionmethanol and NH silica gel were added to the residue and methanol
  4. distillationwas distilled off
  5. additionThe mixture of the reaction mixture and NH silica gel
  6. customwas purified by silica gel column chromatography (NH silica gel: 200 g, elution solvent: ethyl acetate/heptane=1/1 to 4/1→methanol/ethyl acetate=1/9 to 1/4)

출처 및 근거

ORD 기록
ord-116f90953e3d481eaaea2903b96141af
출처 데이터셋
uspto-grants-2008_09
특허 번호
US07425634B2

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