3-Ethyl-1-pentyn-3-ol → 4-{1-Ethyl-1-[4-(3-ethyl-3-hydroxy-1-pentynyl)-3-methyl-phenyl]-propyl}-2,6-dimethyl-phenol

HRID 546872

反応式

HRID 546872 の反応式
[CH2:1]([C:3]([OH:8])([CH2:6][CH3:7])[C:4]#[CH:5])[CH3:2].Br[C:10]1[CH:15]=[CH:14][C:13]([C:16]([C:21]2[CH:26]=[C:25]([CH3:27])[C:24]([OH:28])=[C:23]([CH3:29])[CH:22]=2)([CH2:19][CH3:20])[CH2:17][CH3:18])=[CH:12][C:11]=1[CH3:30].C(=O)(O)[O-].[Na+]>C(N(CC)CC)C.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2].[Cu]I>[CH2:17]([C:16]([C:21]1[CH:22]=[C:23]([CH3:29])[C:24]([OH:28])=[C:25]([CH3:27])[CH:26]=1)([C:13]1[CH:14]=[CH:15][C:10]([C:5]#[C:4][C:3]([CH2:6][CH3:7])([OH:8])[CH2:1][CH3:2])=[C:11]([CH3:30])[CH:12]=1)[CH2:19][CH3:20])[CH3:18]

参加物

7

反応物 3

HCID 226983-Ethyl-1-pentyn-3-olHCID 516892Sodium BicarbonateHCID 574847624-[1-(4-Bromo-3-methyl-phenyl)-1-ethyl-propyl]-2,6-dimethyl-phenol

生成物 1

HCID 574434904-{1-Ethyl-1-[4-(3-ethyl-3-hydroxy-1-pentynyl)-3-methyl-phenyl]-propyl}-2,6-dimethyl-phenol収率 97.3%

試薬・触媒・溶媒 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)触媒HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)触媒HCID 8471Triethylamine溶媒

反応条件

温度
160 °C

実験手順

3-Ethyl-1-pentyn-3-ol (1.4 mL, 10.88 mmol), a [1,1′-bis(diphenylphosphino)ferrocene]dichloropalladium (II), dichloromethane complex (1:1) (592 mg, 0.725 mmol) and copper (I) iodide (138 mg, 0.725 mmol) were added to a solution of 4-[1-(4-bromo-3-methyl-phenyl)-1-ethyl-propyl]-2,6-dimethyl-phenol (Example 38-(2); 2.62 g, 7.25 mmol) in triethylamine (15 mL), and the mixture was stirred with microwave heating at 160° C. for three minutes. The reaction mixture was then poured into a saturated aqueous sodium bicarbonate solution, followed by extraction with dichloromethane. The organic layer was dried over anhydrous magnesium sulfate, filtered and concentrated under reduced pressure. The resulting residue was purified by silica gel chromatography (hexane:ethyl acetate=100:0 to 50:50) to give the target compound as a colorless oil (2.77 g, 97%).

後処理

  1. extractionfollowed by extraction with dichloromethane
  2. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure
  5. customThe resulting residue was purified by silica gel chromatography (hexane:ethyl acetate=100:0 to 50:50)

出典と根拠

ORDレコード
ord-38791df545b54e439e3846c631a476c7
出典データセット
uspto-grants-2011_05
特許番号
US07935688B2

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