Water → 4-(4-Ethoxyphenyl)pyridine

HRID 1617313

反応式

HRID 1617313 の反応式
C(=O)([O-])[O-].[Na+].[Na+].[N:7]1[CH:12]=[CH:11][C:10](B(O)O)=[CH:9][CH:8]=1.[CH2:16]([O:18][C:19]1[CH:24]=[CH:23][C:22](I)=[CH:21][CH:20]=1)[CH3:17].O>O1CCOCC1.CO>[CH2:16]([O:18][C:19]1[CH:24]=[CH:23][C:22]([C:10]2[CH:11]=[CH:12][N:7]=[CH:8][CH:9]=2)=[CH:21][CH:20]=1)[CH3:17]

参加物

7

反応物 4

HCID 962WaterHCID 10340Sodium CarbonateHCID 2207001-Ethoxy-4-iodobenzeneHCID 2734379(Pyridin-4-yl)boronic acid

生成物 1

HCID 707009334-(4-Ethoxyphenyl)pyridine

試薬・触媒・溶媒 2

HCID 887Methanol溶媒HCID 312751,4-Dioxane溶媒

実験手順

Under inert gas atmosphere 88 mg (0.12 mmol) PdCl2(dppf)xCH2Cl2, 13.6 mL (27.2 mmol) 2N sodium carbonate solution and 1.64 g (13.3 mmol) pyridine-4-boronic acid are added to 3.00 g (12.1 mmol) 1-ethoxy-4-iodo-benzene in 18 mL 1,4-dioxane and 6 mL methanol. The mixture is stirred for 2 d at reflux. After that time, water is added. The precipitate is filtered off, taken up in DCM and extracted with water. The organic layer is dried over sodium sulphate and the solvent is evaporated. The residue is purified by column chromatography (silica gel; gradient DCM:MeOH 100:0→95:5) to yield the desired product which is directly used in the next reaction step.

後処理

  1. temperatureat reflux
  2. filtrationThe precipitate is filtered off
  3. extractionextracted with water
  4. dry with materialThe organic layer is dried over sodium sulphate
  5. customthe solvent is evaporated
  6. customThe residue is purified by column chromatography (silica gel; gradient DCM:MeOH 100:0→95:5)

出典と根拠

ORDレコード
ord-71ae10d6a4d24a50bd57f81488ef55cf
出典データセット
uspto-grants-2014_07
特許番号
US08765959B2

関連ノート

読み込み中…