1-Ethynylcyclohexanol → 4-{1-Ethyl-1-[4-(1-hydroxy-cyclohexylethynyl)-3-methyl-phenyl]-propyl}-2-methyl-phenol

HRID 546865ノート

反応式

HRID 546865 の反応式
C(N(CC)CC)C.[CH2:8]([C:10]([C:21]1[CH:26]=[CH:25][C:24](OS(C(F)(F)F)(=O)=O)=[C:23]([CH3:35])[CH:22]=1)([C:13]1[CH:18]=[CH:17][C:16]([OH:19])=[C:15]([CH3:20])[CH:14]=1)[CH2:11][CH3:12])[CH3:9].[C:36]([C:38]1([OH:44])[CH2:43][CH2:42][CH2:41][CH2:40][CH2:39]1)#[CH:37]>C(#N)C>[CH2:8]([C:10]([C:13]1[CH:18]=[CH:17][C:16]([OH:19])=[C:15]([CH3:20])[CH:14]=1)([C:21]1[CH:26]=[CH:25][C:24]([C:37]#[C:36][C:38]2([OH:44])[CH2:43][CH2:42][CH2:41][CH2:40][CH2:39]2)=[C:23]([CH3:35])[CH:22]=1)[CH2:11][CH3:12])[CH3:9]

参加物

5

反応物 3

HCID 65251-EthynylcyclohexanolHCID 8471TriethylamineHCID 58598300Trifluoromethanesulfonic acid 4-[1-ethyl-1-(4-hydroxy-3-methyl-phenyl)-propyl]-2-methyl-phenyl ester

生成物 1

HCID 574834104-{1-Ethyl-1-[4-(1-hydroxy-cyclohexylethynyl)-3-methyl-phenyl]-propyl}-2-methyl-phenol収率 63.3%

試薬・触媒・溶媒 1

HCID 6342Acetonitrile溶媒

反応条件

温度
110 °C

実験手順

Triethylamine (8.0 mL, 57.6 mmol), tetrakistriphenylphosphine palladium (2.2 g, 1.92 mmol) and cuprous iodide (0.36 g, 1.92 mmol) were added to a solution of trifluoromethanesulfonic acid 4-[1-ethyl-1-(4-hydroxy-3-methyl-phenyl)-propyl]-2-methyl-phenyl ester (Example 1-(1); 8.0 g, 19.2 mmol) and 1-ethynyl-cyclohexanol (3.5 g, 28.8 mmol) in acetonitrile (96 mL), and the mixture was stirred at 110° C. for 1.5 hours. The reaction mixture was extracted with ethyl acetate. The organic layer was washed with water and then dried over anhydrous sodium sulfate and concentrated under reduced pressure. The residue was purified by silica gel chromatography (hexane/ethyl acetate=4/1) to give the title compound (4.75 g, 63%).

後処理

  1. extractionThe reaction mixture was extracted with ethyl acetate
  2. washThe organic layer was washed with water
  3. dry with materialdried over anhydrous sodium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by silica gel chromatography (hexane/ethyl acetate=4/1)

出典と根拠

ORDレコード
ord-f715c8bfc543423595a8c0a298881547
出典データセット
uspto-grants-2011_05
特許番号
US07935688B2

反応ノート

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