Potassium Carbonate → 3-((E)-Hex-2-enyl)-3-methyl-2,3-dihydro-benzofuran-6-carboxylic acid methyl ester

HRID 2092990ノート

反応式

HRID 2092990 の反応式
[CH3:1][O:2][C:3](=[O:16])[C:4]1[CH:9]=[CH:8][C:7](I)=[C:6]([O:11][CH2:12][C:13]([CH3:15])=[CH2:14])[CH:5]=1.C(=O)([O-])[O-].[K+].[K+].[CH:23](B(O)O)=[CH:24][CH2:25][CH2:26][CH3:27]>CN(C=O)C.[Cl-].C([N+](CCCC)(CCCC)CCCC)CCC.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[CH3:1][O:2][C:3]([C:4]1[CH:9]=[CH:8][C:7]2[C:13]([CH2:15]/[CH:23]=[CH:24]/[CH2:25][CH2:26][CH3:27])([CH3:14])[CH2:12][O:11][C:6]=2[CH:5]=1)=[O:16]

参加物

7

反応物 3

HCID 11430Potassium CarbonateHCID 27346091-Pentenylboronic acidHCID 251290454-Iodo-3-(2-methyl-allyloxy)-benzoic acid methyl ester

生成物 1

HCID 684812333-((E)-Hex-2-enyl)-3-methyl-2,3-dihydro-benzofuran-6-carboxylic acid methyl ester

試薬・触媒・溶媒 3

HCID 70681Tetrabutylammonium Chloride触媒HCID 167845palladium(II) acetate触媒HCID 6228Dimethylformamide溶媒2 回

反応条件

温度
160 °C

実験手順

To a solution of 4-Iodo-3-(2-methyl-allyloxy)-benzoic acid methyl ester (65 mg, 0.2 mmol) in DMF (2 mL) were added Potassium carbonate (54 mg, 0.39 mmol), Tetrabutylammonium chloride (54 mg, 0.2 mmol), Palladium acetate (3.5 mg, 0.02 mmol) in DMF (5 mL) and 1-Penten-1-ylboronic acid, (26 mg, 0.23 mmol). The resulting mixture was stirred under microwave irradiation (160° C., 15 min), cooled to room temperature, filtered over silica, washed with water, dried over MgSO4 and concentrated. Column chromatography (silica gel, heptane/CH2Cl2: 4/6) afforded title compound as a slightly colorless oil.

後処理

  1. temperaturecooled to room temperature
  2. filtrationfiltered over silica
  3. washwashed with water
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated

出典と根拠

ORDレコード
ord-81fb000a019a4244b00f562b18a2be2d
出典データセット
uspto-grants-2013_05
特許番号
US08440832B2

反応ノート

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