Water → ethyl 1-benzyl-4-nitro-1H-pyrrole-2-carboxylate

HRID 453577

반응식

HRID 453577 반응식
[N+:1]([C:4]1[CH:5]=[C:6]([C:9]([O:11][CH2:12][CH3:13])=[O:10])[NH:7][CH:8]=1)([O-:3])=[O:2].[H-].[Na+].[CH2:16](Br)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.O>CN(C)C=O>[CH2:16]([N:7]1[CH:8]=[C:4]([N+:1]([O-:3])=[O:2])[CH:5]=[C:6]1[C:9]([O:11][CH2:12][CH3:13])=[O:10])[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

참가 물질

6

반응물 4

HCID 962WaterHCID 7498Benzyl BromideHCID 24758Sodium hydrideHCID 242169Ethyl 4-Nitropyrrole-2-carboxylate

생성물 1

HCID 284071ethyl 1-benzyl-4-nitro-1H-pyrrole-2-carboxylate수율 97%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

To a solution of ethyl 4-nitro-1H-pyrrole-2-carboxylate (10 g) in N,N-dimethylformamide (100 mL) was slowly added sodium hydride (60%, oily, 2.4 g) at 0° C., and the mixture was stirred at room temperature for 30 min. Benzylbromide (8.0 mL) was slowly added to the reaction mixture, and the mixture was stirred at room temperature for 2 hr. Water was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The ethyl acetate layer was washed with saturated brine, dried (MgSO4) and concentrated. The obtained residue was subjected to silica gel column chromatography to give ethyl 1-benzyl-4-nitro-1H-pyrrole-2-carboxylate (14.3 g, yield 97%) as yellow crystals from a fraction eluted with ethyl acetate-hexane (1:3, volume ratio). melting point 73° C.

후처리

  1. customat 0° C.
  2. stirringthe mixture was stirred at room temperature for 2 hr
  3. extractionthe mixture was extracted with ethyl acetate
  4. washThe ethyl acetate layer was washed with saturated brine
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated

출처 및 근거

ORD 기록
ord-8db193479ca94788aeda11e3d5bee62d
출처 데이터셋
uspto-grants-2013_07
특허 번호
US08492405B2

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