Sodium hydride → 1-(Cyclopropylmethyl)-1H-pyrazole-4-carboxaldehyde

HRID 220483ノート

反応式

HRID 220483 の反応式
[NH:1]1[CH:5]=[C:4]([CH:6]=[O:7])[CH:3]=[N:2]1.[H-].[Na+].Br[CH2:11][CH:12]1[CH2:14][CH2:13]1>CN(C=O)C>[CH:12]1([CH2:11][N:1]2[CH:5]=[C:4]([CH:6]=[O:7])[CH:3]=[N:2]2)[CH2:14][CH2:13]1

参加物

5

反応物 3

HCID 24758Sodium hydrideHCID 81503BromomethylcyclopropaneHCID 51306731H-pyrazole-4-carbaldehyde

生成物 1

HCID 627265101-(Cyclopropylmethyl)-1H-pyrazole-4-carboxaldehyde

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 1H-pyrazole-4-carbaldehyde (0.200 g, 2.08 mmol) to a suspension of sodium hydride (0.092 g, 2.29 mmol) in DMF (3 mL) at 0° C. Stir for 20 min. at 0° C. Add a solution of 1-(bromomethyl)cyclopropane (0.295 g, 2.18 mmol) in DMF (4 mL) dropwise to the reaction mixture. Stir reaction to ambient temperature for 18 hr. Quench with aqueous saturated sodium bicarbonate solution and add ethyl acetate. Separate organic layer. Extract aqueous layer twice with ethyl acetate, dry combined organics (magnesium sulfate), filter, concentrate and purify (silica gel chromatography, eluting with 0:100 to 60:40 ethyl acetate:hexanes) to give the title preparation (175 mg, 56%). GC-MS: m/z=150 [M+].

後処理

  1. stirringStir
  2. customreaction to ambient temperature for 18 hr
  3. customQuench with aqueous saturated sodium bicarbonate solution
  4. additionadd ethyl acetate
  5. dry with materialExtract aqueous layer twice with ethyl acetate, dry combined organics (magnesium sulfate)
  6. filtrationfilter
  7. concentrationconcentrate
  8. custompurify
  9. wash(silica gel chromatography, eluting with 0:100 to 60:40 ethyl acetate:hexanes)
  10. customto give the title
  11. custompreparation (175 mg, 56%)

出典と根拠

ORDレコード
ord-5c741acd0a6c40dc8322e9cafc3c3750
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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