Benzophenone imine → 7-(Benzhydrylideneamino)-3-(4-chlorophenyl)-2-isopropyl-8-methoxy-chromen-4-one

HRID 14468

反応式

HRID 14468 の反応式
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:17](=[O:18])[C:16]3[C:11](=[C:12]([O:27][CH3:28])[C:13](OS(C(F)(F)F)(=O)=O)=[CH:14][CH:15]=3)[O:10][C:9]=2[CH:29]([CH3:31])[CH3:30])=[CH:4][CH:3]=1.CC(C)([O-])C.[Na+].[C:38](=[NH:51])([C:45]1[CH:50]=[CH:49][CH:48]=[CH:47][CH:46]=1)[C:39]1[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=1>C1(C)C=CC=CC=1.C1(P(C2C=CC=CC=2)[C-]2C=CC=C2)C=CC=CC=1.[C-]1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=C1.[Fe+2].C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[C:38](=[N:51][C:13]1[C:12]([O:27][CH3:28])=[C:11]2[C:16]([C:17](=[O:18])[C:8]([C:5]3[CH:6]=[CH:7][C:2]([Cl:1])=[CH:3][CH:4]=3)=[C:9]([CH:29]([CH3:30])[CH3:31])[O:10]2)=[CH:15][CH:14]=1)([C:45]1[CH:46]=[CH:47][CH:48]=[CH:49][CH:50]=1)[C:39]1[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=1

参加物

7

反応物 3

HCID 136809Benzophenone imineHCID 23676156Sodium t-butoxideHCID 86625609Trifluoromethanesulfonic acid 3-(4-chlorophenyl)-2-isopropyl-8-methoxy-4-oxo-4H-chromen-7-yl ester

生成物 1

HCID 866256107-(Benzhydrylideneamino)-3-(4-chlorophenyl)-2-isopropyl-8-methoxy-chromen-4-one

試薬・触媒・溶媒 3

HCID 635956Ferrocene-1,1'-bis-(diphenylphosphine)触媒HCID 9811564Bis(dibenzylideneacetone)palladium触媒HCID 1140Toluene溶媒

反応条件

温度
130 °C

実験手順

A stirred mixture of trifluoromethanesulfonic acid 3-(4-chlorophenyl)-2-isopropyl-8-methoxy-4-oxo-4H-chromen-7-yl ester (2.41 g, 5.05 mmol), 1,1′-bis(diphenylphosphino)-ferrocene (5.6 g, 10.1 mmol, 2 eq.), tris(dibenzylideneacetone)dipalladium (0) (3.08 g, 3.36 mmol, 0.665 eq.), sodium t-butoxide (0.58 g, 6.06 mmol, 1.2 eq.) and benzophenone-imine (1.1 g, 1.02 ml, 6.06 mmol, 1.2 eq.) in toluene (160 ml) is heated under reflux at 130° C. for 45 min. The reaction mixture is allowed to cool to room temperature and filtered through a pad of Celite filter aid. The Celite is washed with methylene chloride, and the filtrate is evaporated to dryness in vacuo to afford 7-(benzhydrylideneamino)-3-(4-chlorophenyl)-2-isopropyl-8-methoxy-chromen-4-one as a red oil. A stirred solution of the red oil in tetrahydrofuran (80 ml) is treated with 2M HCl solution (80 ml). After 30 min, the reaction mixture is basified with 17% ammonia solution and washed with ethyl acetate. The organic layer is dried over anhydrous magnesium sulfate and filtered, and the solvent is removed by evaporation in vacuo to afford a dark residue. This is purified by flash chromatography (cyclohexane/ethyl acetate=9:1) to afford the title compound.

後処理

  1. temperatureis heated
  2. temperatureto cool to room temperature
  3. filtrationfiltered through a pad of Celite
  4. filtrationfilter aid
  5. washThe Celite is washed with methylene chloride
  6. customthe filtrate is evaporated to dryness in vacuo

出典と根拠

ORDレコード
ord-115bc09d2feb474a8428d3de13c2fd10
出典データセット
uspto-grants-2010_06
特許番号
US07732435B2

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