Ethyl 6-methoxy-1-oxo-3-phenyl-1H-indene-2-carboxylate → 1-hydroxy-6-methoxy-1-(3-methoxy-phenyl)-3-phenyl-1H-indene-2-carboxylic acid ethyl ester

HRID 19524

反応式

HRID 19524 の反応式
[CH2:1]([O:3][C:4]([C:6]1[C:7](=[O:23])[C:8]2[C:13]([C:14]=1[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)=[CH:12][CH:11]=[C:10]([O:21][CH3:22])[CH:9]=2)=[O:5])[CH3:2].[CH3:24][O:25][C:26]1[CH:27]=[C:28]([Mg]Br)[CH:29]=[CH:30][CH:31]=1>C1COCC1>[CH2:1]([O:3][C:4]([C:6]1[C:7]([OH:23])([C:30]2[CH:29]=[CH:28][CH:27]=[C:26]([O:25][CH3:24])[CH:31]=2)[C:8]2[C:13]([C:14]=1[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)=[CH:12][CH:11]=[C:10]([O:21][CH3:22])[CH:9]=2)=[O:5])[CH3:2]

参加物

4

反応物 2

HCID 23249734Ethyl 6-methoxy-1-oxo-3-phenyl-1H-indene-2-carboxylateHCID 178490745HCID 178490745、化合物

生成物 1

HCID 115245071-hydroxy-6-methoxy-1-(3-methoxy-phenyl)-3-phenyl-1H-indene-2-carboxylic acid ethyl ester収率 90.4%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

反応条件

温度
0 °C

実験手順

6-Methoxy-1-oxo-3-phenyl-1H-indene-2-carboxylic acid ethyl ester (100 mg, 0.325 mmol) obtained in Example 1 was dissolved in THF and 1.5 equivalents of 3-methoxyphenylmagnesium bromide were added thereto, followed by stirring for 1 hr at 0° C. Then, the reaction mixture washed with saturated saline and extracted with ethyl acetate. The organic layer was separated, dried over anhydrous MgSO4, and concentrated under a reduced pressure. The resulting residue was purified by flash chromatography to obtain 122 mg of the titled compound (yield: 90.4%).

後処理

  1. washThen, the reaction mixture washed with saturated saline
  2. extractionextracted with ethyl acetate
  3. customThe organic layer was separated
  4. dry with materialdried over anhydrous MgSO4
  5. concentrationconcentrated under a reduced pressure
  6. customThe resulting residue was purified by flash chromatography

出典と根拠

ORDレコード
ord-561fdd55bd744beb8d9bda76c4e9af68
出典データセット
uspto-grants-2010_06
特許番号
US07745439B2

関連ノート

読み込み中…