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

Reaktionsgleichung

Reaktionsgleichung von HRID 546872
[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]

Komponenten

7

Edukt 3

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

Produkt 1

HCID 574434904-{1-Ethyl-1-[4-(3-ethyl-3-hydroxy-1-pentynyl)-3-methyl-phenyl]-propyl}-2,6-dimethyl-phenolAusbeute 97,3 %

Reagenzien, Katalysatoren, Lösungsmittel 3

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

Reaktionsbedingungen

Temperatur
160 °C

Versuchsvorschrift

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%).

Aufarbeitung

  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)

Quellen und Nachweise

ORD-Eintrag
ord-38791df545b54e439e3846c631a476c7
Quelldatensatz
uspto-grants-2011_05
Patentnummer
US07935688B2

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