Sodium Carbonate → 4-(4'-Methoxy-biphenyl-4-yl)4-oxo-butyric acid, methyl ester

HRID 381838

反応式

HRID 381838 の反応式
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6](B(O)O)=[CH:5][CH:4]=1.Br[C:13]1[CH:18]=[CH:17][C:16]([C:19](=[O:26])[CH2:20][CH2:21][C:22]([O:24][CH3:25])=[O:23])=[CH:15][CH:14]=1.C(=O)([O-])[O-].[Na+].[Na+]>C1(C)C=CC=CC=1.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:13]2[CH:14]=[CH:15][C:16]([C:19](=[O:26])[CH2:20][CH2:21][C:22]([O:24][CH3:25])=[O:23])=[CH:17][CH:18]=2)=[CH:5][CH:4]=1

参加物

6

反応物 3

HCID 10340Sodium CarbonateHCID 201262(4-Methoxyphenyl)boronic acidHCID 838865Methyl 4-(4-bromophenyl)-4-oxobutanoate

生成物 1

HCID 5273114-(4'-Methoxy-biphenyl-4-yl)4-oxo-butyric acid, methyl ester

試薬・触媒・溶媒 2

HCID 178418397HCID 178418397、化合物触媒HCID 1140Toluene溶媒

実験手順

In a manner similar to Example 12, Step (b), (4-methoxyphenyl)boronic acid (0.913 g, 0.00601 mol) was allowed to react with 4-(4-bromo-phenyl)-4-oxo-butyric acid, methyl ester (1.356 g, 0.00500 mol) in the presence of tetrakis(triphenylphosphine)palladium(0) (0.173 g, 0.000150 mol) and 2.0 M aqueous sodium carbonate (5.0 mL, 0.010 mol) in toluene (10 mL) to give, after chromatography on silica gel (270 g, 230-400 mesh), eluting with dichloromethane (15×250 mL); dichloromethane-methanol (100:1, 19×225 mL; 50:1, 5×225 mL), 1.386 g of 4-(4′-methoxy-biphenyl-4-yl)-4-oxo-butyric acid, methyl ester as a white solid; mp 96.0-100.5° C.

後処理

  1. customto give
  2. washafter chromatography on silica gel (270 g, 230-400 mesh), eluting with dichloromethane (15×250 mL)

出典と根拠

ORDレコード
ord-4ec26f4204b241a9babdb3aa68ba0ebd
出典データセット
uspto-grants-2001_10
特許番号
US06307089B2

関連ノート

読み込み中…