Triethylamine → 2-Methoxy-1-(4-methoxyphenoxy)-4-propylbenzene

HRID 1023908

Reaktionsgleichung

Reaktionsgleichung von HRID 1023908
[CH3:1][O:2][C:3]1[CH:8]=[C:7]([CH2:9][CH2:10][CH3:11])[CH:6]=[CH:5][C:4]=1[OH:12].[CH3:13][O:14][C:15]1[CH:20]=[CH:19][C:18](B(O)O)=[CH:17][CH:16]=1.C(N(CC)CC)C>ClCCl.C([O-])(=O)C.[Cu+2].C([O-])(=O)C>[CH3:1][O:2][C:3]1[CH:8]=[C:7]([CH2:9][CH2:10][CH3:11])[CH:6]=[CH:5][C:4]=1[O:12][C:18]1[CH:19]=[CH:20][C:15]([O:14][CH3:13])=[CH:16][CH:17]=1

Komponenten

6

Edukt 3

HCID 8471TriethylamineHCID 177394-PropylguaiacolHCID 201262(4-Methoxyphenyl)boronic acid

Produkt 1

HCID 247861922-Methoxy-1-(4-methoxyphenoxy)-4-propylbenzene

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 8895Cupric acetateKatalysatorHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

A mixture containing 2-methoxy-4-propylphenol (0.625 mmol; 100 μl), copper(II) acetate (0.625 mmol; 114 mg), 4-methoxyphenylboronic acid (1.25 mmol; 190 mg), triethylamine (3.12 mmol; 0.43 ml), some crushed molecular sieves 4 Å in dichloromethane (3 ml) was stirred at rt under air for 24 h. The residue is filtered with chloroform on Celite. The organic phase is washed with saturated NH4Cl, saturated NaHCO3 and brine. After drying (MgSO4), concentration and purification by preparative TLC on silica gel (ethyl acetate/cyclohexane—20/80), the title compound is collected as a colorless oil (70 mg; 0.26 mmol; 41%).

Aufarbeitung

  1. filtrationThe residue is filtered with chloroform on Celite
  2. washThe organic phase is washed with saturated NH4Cl, saturated NaHCO3 and brine
  3. customAfter drying
  4. concentration(MgSO4), concentration and purification by preparative TLC on silica gel (ethyl acetate/cyclohexane—20/80)
  5. customthe title compound is collected as a colorless oil (70 mg; 0.26 mmol; 41%)

Quellen und Nachweise

ORD-Eintrag
ord-70b6199f952a41498993e72a04618e1a
Quelldatensatz
uspto-grants-2014_05
Patentnummer
US08722746B2

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