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

HRID 1023908

반응식

HRID 1023908 반응식
[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

참가 물질

6

반응물 3

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

생성물 1

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

시약·촉매·용매 2

HCID 8895Cupric acetate촉매HCID 6344Dichloromethane용매

실험 절차

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%).

후처리

  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%)

출처 및 근거

ORD 기록
ord-70b6199f952a41498993e72a04618e1a
출처 데이터셋
uspto-grants-2014_05
특허 번호
US08722746B2

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