Dimethylformamide → Methyl 1-(6-benzyloxy-2-naphthylmethyl)-4-phenylpyrrole-3-carboxylate

HRID 350076노트

반응식

HRID 350076 반응식
[H-].[Na+].[C:3]1([C:9]2[C:10]([C:14]([O:16][CH3:17])=[O:15])=[CH:11][NH:12][CH:13]=2)[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[CH2:18]([O:25][C:26]1[CH:27]=[C:28]2[C:33](=[CH:34][CH:35]=1)[CH:32]=[C:31]([CH2:36]Cl)[CH:30]=[CH:29]2)[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.CN(C)C=O>O>[CH2:18]([O:25][C:26]1[CH:27]=[C:28]2[C:33](=[CH:34][CH:35]=1)[CH:32]=[C:31]([CH2:36][N:12]1[CH:13]=[C:9]([C:3]3[CH:4]=[CH:5][CH:6]=[CH:7][CH:8]=3)[C:10]([C:14]([O:16][CH3:17])=[O:15])=[CH:11]1)[CH:30]=[CH:29]2)[C:19]1[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=1

참가 물질

6

반응물 4

HCID 6228DimethylformamideHCID 24758Sodium hydrideHCID 5142464Methyl 4-phenyl-1H-pyrrole-3-carboxylateHCID 230249106-Benzyloxy-2-chloromethylnaphthalene

생성물 1

HCID 23024964Methyl 1-(6-benzyloxy-2-naphthylmethyl)-4-phenylpyrrole-3-carboxylate수율 80%

시약·촉매·용매 1

HCID 962Water용매

실험 절차

Sodium hydride (60%, oily, 0.36 g) was added to a mixture of methyl 4-phenylpyrrole-3-carboxylate (1.81 g), 6-benzyloxy-2-chloromethylnaphthalene (2.54 g) and N,N-dimethylformamide (35 ml), and the mixture was stirred at room temperature for 30 minutes. The reaction mixture was poured into water, which was extracted with ethyl acetate. The ethyl acetate layer was washed with water, then with saturated aqueous sodium chloride solution, dried (MgSO4), then concentrated. The residue was subjected to silica gel column chromatograpy, and methyl 1-(6-benzyloxy-2-naphthylmethyl)-4-phenylpyrrole-3-carboxylate (3.20 g, yield: 80%) was obtained as colorless crystals from the fraction eluted with tetrahydrofuran-hexane (1:2, volume ratio). This was recrystallized from ethyl acetate-hexane. Melting point: 109–110° C.

후처리

  1. extractionwas extracted with ethyl acetate
  2. washThe ethyl acetate layer was washed with water
  3. dry with materialwith saturated aqueous sodium chloride solution, dried (MgSO4)
  4. concentrationconcentrated

출처 및 근거

ORD 기록
ord-efd2f09126f940b6b60c38a1ec90279e
출처 데이터셋
uspto-grants-2007_02
특허 번호
US07179823B1

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