Cesium carbonate → 1-(4-(4-Isopropoxyphenoxy)-2,6-dimethylphenyl)ethanone

HRID 1465554노트

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HRID 1465554 반응식
Br[C:2]1[CH:7]=[CH:6][C:5]([O:8][CH:9]([CH3:11])[CH3:10])=[CH:4][CH:3]=1.[OH:12][C:13]1[CH:18]=[C:17]([CH3:19])[C:16]([C:20](=[O:22])[CH3:21])=[C:15]([CH3:23])[CH:14]=1.Cl.CN(C)CC(O)=O.C(=O)([O-])[O-].[Cs+].[Cs+]>O1CCOCC1.[Cu](I)I.O>[CH:9]([O:8][C:5]1[CH:6]=[CH:7][C:2]([O:12][C:13]2[CH:14]=[C:15]([CH3:23])[C:16]([C:20](=[O:22])[CH3:21])=[C:17]([CH3:19])[CH:18]=2)=[CH:3][CH:4]=1)([CH3:11])[CH3:10]

참가 물질

8

반응물 4

HCID 10796Cesium carbonateHCID 75605N,N-Dimethylglycine hydrochlorideHCID 2280881-Bromo-4-(propan-2-yloxy)benzeneHCID 40573701-(4-Hydroxy-2,6-dimethylphenyl)ethanone

생성물 1

HCID 866908581-(4-(4-Isopropoxyphenoxy)-2,6-dimethylphenyl)ethanone수율 79%

시약·촉매·용매 3

HCID 83717Copper iodide촉매HCID 962Water용매HCID 312751,4-Dioxane용매

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온도
90 °C

실험 절차

A mixture of 1-bromo-4-isopropoxybenzene (16-3, 3.02 g, 14.0 mmol), 1-(4-hydroxy-2,6-dimethylphenyl)ethanone (4-2, 3.54 g, 21.6 mmol), N,N-dimethylglycine HCl salt (0.50 g, 3.5 mmol), copper iodide (0.34 g, 1.8 mmol), and cesium carbonate (9.08 g, 27.9 mmol) in dioxane (30 mL) was heated at 90° C. for 48 h. The reaction mixture was cooled to room temperature, added with water, and extracted with EtOAc. The organic layer was washed with brine, dried over anhydrous MgSO4, concentrated under reduced pressure, and purified by column chromatography on silica gel (EtOAc:hexanes=1:20 as eluant) to give 1-(4-(4-isopropoxyphenoxy)-2,6-dimethylphenyl)ethanone (16-4, 2.07 g) as white solids in 79% yield: 1H NMR (500 MHz, CDCl3) δ 6.94 (m, 2 H), 6.87 (m, 2 H), 6.58 (s, 2 H), 4.50 (t, J=6.1 Hz, 1 H), 2.46 (s, 3 H), 2.21 (s, 6 H), 1.34 (s, 6 H), 1.26 (m, 3 H), 0.87 (m, 3 H).

후처리

  1. temperatureThe reaction mixture was cooled to room temperature
  2. extractionextracted with EtOAc
  3. washThe organic layer was washed with brine
  4. dry with materialdried over anhydrous MgSO4
  5. concentrationconcentrated under reduced pressure
  6. custompurified by column chromatography on silica gel (EtOAc:hexanes=1:20 as eluant)

출처 및 근거

ORD 기록
ord-b9814368d938440291184dbd068a0a53
출처 데이터셋
uspto-grants-2015_04
특허 번호
US08999983B2

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