1,2-Dimethoxyethane → Ethyl 4-(pyridin-4-yl)benzoate

HRID 278565ノート

反応式

HRID 278565 の反応式
Br[C:2]1[CH:12]=[CH:11][C:5]([C:6]([O:8][CH2:9][CH3:10])=[O:7])=[CH:4][CH:3]=1.B([O-])([O-])O[C:15]1[CH:20]=[CH:19][N:18]=[CH:17][CH:16]=1.C(=O)([O-])O.[Na+].COCCOC>C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.O>[N:18]1[CH:19]=[CH:20][C:15]([C:2]2[CH:12]=[CH:11][C:5]([C:6]([O:8][CH2:9][CH3:10])=[O:7])=[CH:4][CH:3]=2)=[CH:16][CH:17]=1

参加物

7

反応物 4

HCID 80711,2-DimethoxyethaneHCID 22043Ethyl 4-bromobenzoateHCID 516892Sodium BicarbonateHCID 867578874-Pyridyl borate

生成物 1

HCID 15294733Ethyl 4-(pyridin-4-yl)benzoate収率 56.3%

試薬・触媒・溶媒 2

HCID 178418397HCID 178418397、化合物触媒HCID 962Water溶媒

実験手順

To a mixture of ethyl 4-bromobenzoate (2.29 g), 4-pyridyl borate (1.23 g), 1 M sodium hydrogen carbonate solution (30 ml) and 1,2-dimethoxyethane (40 ml) was added tetrakis(triphenylphosphine)palladium (0.3 g) and the mixture was stirred for 3 hours with reflux under nitrogen atmosphere. To the mixture was added water and the solution was extracted with ethyl acetate. The extract was washed with water, dried (MgSO4) and concentrated. The residue was subjected to silica gel chromatography, and eluted with hexane-ethyl acetate (2:1) to give the title compound as crystals (1.15 g, 50.7%).

後処理

  1. temperaturewith reflux under nitrogen atmosphere
  2. extractionthe solution was extracted with ethyl acetate
  3. washThe extract was washed with water
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated
  6. washeluted with hexane-ethyl acetate (2:1)

出典と根拠

ORDレコード
ord-08186b392d05445ba3a70fe0619d71c2
出典データセット
uspto-grants-2002_03
特許番号
US06359134B1

反応ノート

読み込み中…