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

HRID 546865노트

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HRID 546865 반응식
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]

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 6342Acetonitrile용매

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온도
110 °C

실험 절차

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%).

후처리

  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)

출처 및 근거

ORD 기록
ord-f715c8bfc543423595a8c0a298881547
출처 데이터셋
uspto-grants-2011_05
특허 번호
US07935688B2

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