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

HRID 1465554ノート

反応式

HRID 1465554 の反応式
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]

参加物

8

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 3

HCID 83717Copper iodide触媒HCID 962Water溶媒HCID 312751,4-Dioxane溶媒

反応条件

温度
90 °C

実験手順

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).

後処理

  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)

出典と根拠

ORDレコード
ord-b9814368d938440291184dbd068a0a53
出典データセット
uspto-grants-2015_04
特許番号
US08999983B2

反応ノート

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