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

HRID 546858ノート

反応式

HRID 546858 の反応式
C(N(CC)CC)C.[C:8]([C:10]1([OH:15])[CH2:14][CH2:13][CH2:12][CH2:11]1)#[CH:9].[CH2:16]([C:18]([C:29]1[CH:34]=[CH:33][C:32](OS(C(F)(F)F)(=O)=O)=[C:31]([CH3:43])[CH:30]=1)([C:21]1[CH:26]=[CH:25][C:24]([OH:27])=[C:23]([CH3:28])[CH:22]=1)[CH2:19][CH3:20])[CH3:17].C(OCC)(=O)C>C(#N)C.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>[CH2:16]([C:18]([C:21]1[CH:26]=[CH:25][C:24]([OH:27])=[C:23]([CH3:28])[CH:22]=1)([C:29]1[CH:34]=[CH:33][C:32]([C:9]#[C:8][C:10]2([OH:15])[CH2:14][CH2:13][CH2:12][CH2:11]2)=[C:31]([CH3:43])[CH:30]=1)[CH2:19][CH3:20])[CH3:17]

参加物

7

反応物 4

HCID 8471TriethylamineHCID 8857Ethyl AcetateHCID 870741-EthynylcyclopentanolHCID 58598300Trifluoromethanesulfonic acid 4-[1-ethyl-1-(4-hydroxy-3-methyl-phenyl)-propyl]-2-methyl-phenyl ester

生成物 1

HCID 574833964-{1-Ethyl-1-[4-(1-hydroxy-cyclopentylethynyl)-3-methyl-phenyl]-propyl}-2-methyl-phenol収率 64%

試薬・触媒・溶媒 2

HCID 178418397HCID 178418397、化合物触媒HCID 6342Acetonitrile溶媒

反応条件

温度
110 °C

実験手順

Triethylamine (5.2 mL, 37.3 mmol), 1-ethynylcyclopentanol (2 g, 18.2 mmol), cuprous iodide (0.24 g, 1.26 mmol) and tetrakis(triphenylphosphine)palladium (0) (1.44 g, 1.25 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); 5.2 g, 12.5 mmol) in acetonitrile (52 mL) in a nitrogen atmosphere at room temperature, and the mixture was stirred at 110° C. for four hours. Ethyl acetate was added to the residue. The organic layer was washed with water and brine and then dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was purified by silica gel chromatography (hexane only to hexane/ethyl acetate=4/1) to give the title compound (3 g, 64%).

後処理

  1. washThe organic layer was washed with water and brine
  2. dry with materialdried over anhydrous magnesium sulfate
  3. concentrationconcentrated under reduced pressure
  4. customThe residue was purified by silica gel chromatography (hexane only to hexane/ethyl acetate=4/1)

出典と根拠

ORDレコード
ord-845aa288cf8c49c991f45d790fb81d9c
出典データセット
uspto-grants-2011_05
特許番号
US07935688B2

反応ノート

読み込み中…