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

HRID 220481노트

반응식

HRID 220481 반응식
[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

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 6228Dimethylformamide용매2회

반응 조건

온도
0 °C

실험 절차

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+].

후처리

  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%)

출처 및 근거

ORD 기록
ord-b49960dd7d97476f83026d6423df702e
출처 데이터셋
uspto-grants-2012_06
특허 번호
US08202873B2

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