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

HRID 625998

反応式

HRID 625998 の反応式
[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

参加物

6

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 8895Cupric acetate触媒HCID 6344Dichloromethane溶媒

実験手順

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%).

後処理

  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%)

出典と根拠

ORDレコード
ord-73d0fe35e6b1435a91a548055e4dadb1
出典データセット
uspto-grants-2016_04
特許番号
US09309179B2

関連ノート

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