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Tetrahydrofuran → (E)-(4-methoxyphenyl)(4-styrylquinolin-6-yl)methanone

HRID 1778301
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HRID 1778301 반응식
CON(C)[C:4]([C:6]1[CH:7]=[C:8]2[C:13](=[CH:14][CH:15]=1)[N:12]=[CH:11][CH:10]=[C:9]2/[CH:16]=[CH:17]/[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)=[O:5].Cl[C:26]1[CH:31]=[CH:30][C:29]([Mg]Br)=[CH:28][CH:27]=1.C1C[O:37][CH2:36]C1>C(Cl)Cl.O>[CH3:36][O:37][C:26]1[CH:31]=[CH:30][C:29]([C:4]([C:6]2[CH:7]=[C:8]3[C:13](=[CH:14][CH:15]=2)[N:12]=[CH:11][CH:10]=[C:9]3/[CH:16]=[CH:17]/[C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)=[O:5])=[CH:28][CH:27]=1
참가 물질반응 조건실험 절차후처리출처 및 근거반응 노트

참가 물질

6

반응물 3

HCID 8028TetrahydrofuranHCID 118323977(E)-N-methoxy-N-methyl-4-styrylquinoline-6-carboxamideHCID 178478191HCID 178478191, 화합물

생성물 1

HCID 118324021(E)-(4-methoxyphenyl)(4-styrylquinolin-6-yl)methanone

시약·촉매·용매 2

HCID 962Water용매HCID 6344Dichloromethane
용매

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온도
0 °C

실험 절차

To a solution of (E)-N-methoxy-N-methyl-4-styrylquinoline-6-carboxamide (150 mg, 0.47 mmol) in anhydrous THF (2 mL) was dropwise added dropwise (4-chlorophenyl)magnesium bromide (0.5 M, 1.23 mL, 0.61 mmol) at 0° C. under N2 and the resulting reaction mixture was stirred at 0° C. for 3 hr. The reaction was diluted with CH2Cl2 and water. The aqueous layer was extracted with CH2Cl2 and the combined organics were concentrated and purified by chromatography (15-20% EtOAc/hexanes) to yield (E)-(4-methoxyphenyl)(4-styrylquinolin-6-yl)methanone. (ES, m/z) 366.0 [M+H]+

후처리

  1. customthe resulting reaction mixture
  2. extractionThe aqueous layer was extracted with CH2Cl2
  3. concentrationthe combined organics were concentrated
  4. custompurified by chromatography (15-20% EtOAc/hexanes)

출처 및 근거

ORD 기록
ord-f32d476cf65b469093d52d3fb152349e
출처 데이터셋
uspto-grants-2016_02
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09266835B2

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