4'-Hydroxyacetophenone → 1-[4-(Quinolin-2-ylmethoxy)-phenyl]-ethanone

HRID 33839

반응식

HRID 33839 반응식
Cl[CH2:2][C:3]1[CH:12]=[CH:11][C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[N:4]=1.[CH3:13][C:14]([C:16]1[CH:17]=[CH:18][C:19]([OH:22])=[CH:20][CH:21]=1)=[O:15].C(=O)([O-])[O-].[K+].[K+].[OH-].[Na+]>CC(C)=O.C(OCC)(=O)C>[N:4]1[C:5]2[C:10](=[CH:9][CH:8]=[CH:7][CH:6]=2)[CH:11]=[CH:12][C:3]=1[CH2:2][O:22][C:19]1[CH:20]=[CH:21][C:16]([C:14](=[O:15])[CH3:13])=[CH:17][CH:18]=1

참가 물질

7

반응물 4

HCID 74694'-HydroxyacetophenoneHCID 11430Potassium CarbonateHCID 14798Sodium HydroxideHCID 203942-(Chloromethyl)quinoline

생성물 1

HCID 287750621-[4-(Quinolin-2-ylmethoxy)-phenyl]-ethanone수율 71%

시약·촉매·용매 2

HCID 180Acetone용매HCID 8857Ethyl Acetate용매

반응 조건

온도
60 °C

실험 절차

To a solution of 2-Chloromethyl quinoline (2.5 g, 14 mmole) in acetone (47 ml) was added 4-hydroxy acetophenone (1.92 g, 1.0 eq.) and potassium carbonate (2.5 g, 2 eq.). The reaction mixture was heated at 60° C. for 16 h under N2 atmosphere, cooled to ambient temperature and poured into 1N sodium hydroxide (50 ml)/ethyl acetate (100 ml). The layers were separated and the organic layer dried magnesium sulfate, filtered and concentrated. Biotage MPLC was run using a 5-40% ethyl acetate/hexane gradient on a 40 M column to provide the title compound as a white solid (2.75 g, 71%). 1H NMR (400 MHz, CDCl3) δ 8.19 (d, J=8.7 Hz, 1 H), 8.07 (d, J=8.7, 1H), 7.91 (m, 2H), 7.82 (dd, J=8.3, 1.3 1H), 7.73 (t, J=7.1 Hz, 1 H), 7.62 (d, J =8.3 Hz, 1 H), 7.54 (t, J=7.1 Hz, 1 H), 7.06 (m, 2H), 5.42 (s, 2 H), 2.51 (s, 3 H); MS: (M+H m/z=278.3).

후처리

  1. temperaturecooled to ambient temperature
  2. customThe layers were separated
  3. filtrationthe organic layer dried magnesium sulfate, filtered
  4. concentrationconcentrated

출처 및 근거

ORD 기록
ord-e3d391ee773b4109bf609d5f850ae399
출처 데이터셋
uspto-grants-2008_09
특허 번호
US07429665B2

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