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

HRID 31571

反応式

HRID 31571 の反応式
[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

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 679Dimethyl Sulfoxide溶媒

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-116f90953e3d481eaaea2903b96141af
出典データセット
uspto-grants-2008_09
特許番号
US07425634B2

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