Sodium hydride → 1-(3,5-Dimethylisoxazol-4-ylmethyl)-1H-pyrazole-4-carbaldehyde

HRID 220481ノート

反応式

HRID 220481 の反応式
[H-].[Na+].[NH:3]1[CH:7]=[C:6]([CH:8]=[O:9])[CH:5]=[N:4]1.Cl[CH2:11][C:12]1[C:13]([CH3:18])=[N:14][O:15][C:16]=1[CH3:17]>CN(C)C=O>[CH3:18][C:13]1[C:12]([CH2:11][N:3]2[CH:7]=[C:6]([CH:8]=[O:9])[CH:5]=[N:4]2)=[C:16]([CH3:17])[O:15][N:14]=1

参加物

5

反応物 3

HCID 24758Sodium hydrideHCID 88246Isoxazole, 4-(chloromethyl)-3,5-dimethyl-HCID 51306731H-pyrazole-4-carbaldehyde

生成物 1

HCID 866416531-(3,5-Dimethylisoxazol-4-ylmethyl)-1H-pyrazole-4-carbaldehyde

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒2 回

反応条件

温度
0 °C

実験手順

Add N,N-dimethylformamide (3 mL) to sodium hydride (0.092 g, 2.29 mmol) and stir at 0° C. Add 1-H-pyrazole-4-carboxaldehyde (0.200 g, 2.08 mmol) and stir at 0° C. for 20 min. Dissolve 4-chloromethyl-3,5-dimethylisoxazole (0.318 g, 2.18 mmol) in N,N-dimethylformamide (4 mL) and add to reaction mixture. Stir reaction at room temperature for 18 hr. Quench with aqueous saturated sodium bicarbonate solution. Add ethyl acetate and separate organic layer. Extract aqueous layer twice with ethyl acetate. Dry combined organic layers (magnesium sulfate), filter, concentrate and purify (silica gel chromatography, eluting with 25:75 to 75:25 ethyl acetate:hexanes), to give the title preparation (387 mg, 91%). GC-MS: m/z=205 [M+].

後処理

  1. stirringStir
  2. customreaction at room temperature for 18 hr
  3. customQuench with aqueous saturated sodium bicarbonate solution
  4. customAdd ethyl acetate and separate organic layer
  5. customDry
  6. filtrationfilter
  7. concentrationconcentrate
  8. custompurify
  9. wash(silica gel chromatography, eluting with 25:75 to 75:25 ethyl acetate:hexanes)
  10. customto give the title
  11. custompreparation (387 mg, 91%)

出典と根拠

ORDレコード
ord-b49960dd7d97476f83026d6423df702e
出典データセット
uspto-grants-2012_06
特許番号
US08202873B2

反応ノート

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