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

HRID 625998

Reaction equation

HRID 625998 reaction equation
[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

Participants

6

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 2

HCID 8895Cupric acetateCatalystHCID 6344DichloromethaneSolvent

Procedure

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%).

Workup

  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%)

Sources & evidence

ORD record
ord-73d0fe35e6b1435a91a548055e4dadb1
Source dataset
uspto-grants-2016_04
Patent number
US09309179B2

Linked notes

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