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Dimethylformamide → Methyl(6-((1,3-dimethyl-1H-pyrazol-5-yl)methoxy)-4-methyl-1-benzothiophen-3-yl)acetate

HRID 591396
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HRID 591396 반응식
[CH3:1][O:2][C:3](=[O:16])[CH2:4][C:5]1[C:9]2[C:10]([CH3:15])=[CH:11][C:12]([OH:14])=[CH:13][C:8]=2[S:7][CH:6]=1.CN(C=O)C.Cl[CH2:23][C:24]1[N:28]([CH3:29])[N:27]=[C:26]([CH3:30])[CH:25]=1.C([O-])([O-])=O.[K+].[K+]>O>[CH3:1][O:2][C:3](=[O:16])[CH2:4][C:5]1[C:9]2[C:10]([CH3:15])=[CH:11][C:12]([O:14][CH2:23][C:24]3[N:28]([CH3:29])[N:27]=[C:26]([CH3:30])[CH:25]=3)=[CH:13][C:8]=2[S:7][CH:6]=1
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참가 물질

6

반응물 4

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 49612705-(chloromethyl)-1,3-dimethyl-1H-pyrazoleHCID 121001301Methyl(6-hydroxy-4-methyl-1-benzothiophen-3-yl)acetate

생성물 1

HCID 118667002Methyl(6-((1,3-dimethyl-1H-pyrazol-5-yl)methoxy)-4-methyl-1-benzothiophen-3-yl)acetate수율 70.9%

시약·촉매·용매 1

HCID 962
Water
용매

실험 절차

To a mixture of methyl(6-hydroxy-4-methyl-1-benzothiophen-3-yl)acetate (150 mg) and DMF (2 mL) were added 5-(chloromethyl)-1,3-dimethyl-1H-pyrazole (101 mg) and K2CO3 (175 mg) at room temperature. The mixture was stirred at room temperature for 3 h. The mixture was poured into water at room temperature and extracted with EtOAc. The organic layer was separated, washed successively with water and brine, dried over MgSO4 and concentrated in vacuo. The residue was purified by silica gel column chromatography (EtOAc/hexane). The product was crystallized from Et2O-hexane to give the title compound (155 mg).

후처리

  1. extractionextracted with EtOAc
  2. customThe organic layer was separated
  3. washwashed successively with water and brine
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by silica gel column chromatography (EtOAc/hexane)
  7. customThe product was crystallized from Et2O-hexane

출처 및 근거

ORD 기록
ord-c12b281d243d4a5d9ca264a03db09543
출처 데이터셋
uspto-grants-2016_01
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09238639B2

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