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

HRID 220483노트

반응식

HRID 220483 반응식
[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

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 6228Dimethylformamide용매2회

반응 조건

온도
0 °C

실험 절차

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+].

후처리

  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%)

출처 및 근거

ORD 기록
ord-5c741acd0a6c40dc8322e9cafc3c3750
출처 데이터셋
uspto-grants-2012_06
특허 번호
US08202873B2

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