Water → Methyl 1-(4-nitro-1H-pyrazol-1-YL)cyclopropane-1-carboxylate

HRID 714840

반응식

HRID 714840 반응식
[N+:1]([C:4]1[CH:5]=[N:6][NH:7][CH:8]=1)([O-:3])=[O:2].[H-].[Na+].Br[CH:12]([CH2:17][CH2:18]Br)[C:13]([O:15][CH3:16])=[O:14].O>CN(C)C(=O)C>[N+:1]([C:4]1[CH:5]=[N:6][N:7]([C:12]2([C:13]([O:15][CH3:16])=[O:14])[CH2:18][CH2:17]2)[CH:8]=1)([O-:3])=[O:2]

참가 물질

6

반응물 4

HCID 962WaterHCID 163764-nitro-1H-pyrazoleHCID 24758Sodium hydrideHCID 296716Methyl 2,4-dibromobutanoate

생성물 1

HCID 117839997Methyl 1-(4-nitro-1H-pyrazol-1-YL)cyclopropane-1-carboxylate수율 60.7%

시약·촉매·용매 1

HCID 31374Dimethylacetamide용매

실험 절차

To a solution of 4-nitro-1H-pyrazole (3.0 g) in N,N-dimethylacetamide (30 mL) was added sodium hydride (60% in mineral oil, 1.2 g) in an ice bath, and the mixture was stirred at the same temperature for 30 min. To the reaction mixture was added methyl 2,4-dibromobutanoate (6.9 g) in an ice bath, and the mixture was stirred at room temperature for 10 hr. The reaction mixture was poured into water, and the reaction mixture was extracted with ethyl acetate. The obtained organic layer was washed with saturated brine, and dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (hexane/ethyl acetate) to give the title compound (3.4 g).

후처리

  1. stirringthe mixture was stirred at room temperature for 10 hr
  2. extractionthe reaction mixture was extracted with ethyl acetate
  3. washThe obtained organic layer was washed with saturated brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customthe solvent was evaporated under reduced pressure
  6. customThe residue was purified by silica gel column chromatography (hexane/ethyl acetate)

출처 및 근거

ORD 기록
ord-ad62ac64d86040748441e1cc9b288647
출처 데이터셋
uspto-grants-2015_11
특허 번호
US09187453B2

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