HCID 69130598、化合物 → HCID 59645405、化合物

HRID 2253269ノート

反応式

HRID 2253269 の反応式
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:11]=[C:12]([C:16]2[CH:21]=[CH:20][C:19]([O:22][C:23]3[CH:28]=[CH:27][C:26]([CH:29]=[CH:30][C:31]([O:33][CH2:34][CH3:35])=[O:32])=[CH:25][CH:24]=3)=[CH:18][CH:17]=2)[C:13]([OH:15])=[O:14])[CH:6]=[C:7]([O:9][CH3:10])[CH:8]=1>[Pd]>[CH3:10][O:9][C:7]1[CH:6]=[C:5]([CH2:11][CH:12]([C:16]2[CH:21]=[CH:20][C:19]([O:22][C:23]3[CH:24]=[CH:25][C:26]([CH2:29][CH2:30][C:31]([O:33][CH2:34][CH3:35])=[O:32])=[CH:27][CH:28]=3)=[CH:18][CH:17]=2)[C:13]([OH:15])=[O:14])[CH:4]=[C:3]([O:2][CH3:1])[CH:8]=1

参加物

3

反応物 1

HCID 69130598HCID 69130598、化合物

生成物 1

HCID 59645405HCID 59645405、化合物

試薬・触媒・溶媒 1

HCID 23938Palladium触媒

実験手順

3-(3,5-Dimethoxyphenyl)-2-{4-[4-(2-ethoxycarbonylvinyl)-phenoxy]-phenyl}-acrylic acid (4, 2.37 g, 5.0 mmol) was dissolved in a mixture of ethanol-dioxane (2:1, 150 mL), and palladium charcoal (10%, 500 mg) was added. The mixture was stirred under hydrogen for 15 hr. Catalyst was then removed by filtration, and solvent was evaporated under reduced pressure to yield 3-(3,5-dimethoxy-phenyl)-2-{4-[4-(2-ethoxycarbonylethyl)-phenoxy]-phenyl}-propionic acid (18) quantitatively. Urea (0.21 g, 3.58 mmol) was dissolved in sodium ethoxide (2.7 M, 2.2 mL, 5.92 mmol) at 80° C. under argon, and to this a solution of 18 (1.13 g, 2.37 mmol) in anhydrous ethanol (15 mL) was added and heated at this temperature for 13 hr. Ethanol was evaporated under reduced pressure, water (20 mL) was added, acidified to pH 1 by 5% aqueous HCl and extracted with ethyl acetate (50 mL). The organic layer was washed with water (2×25 mL), brine (2×20 mL), dried over anhydrous magnesium sulfate and evaporated. The crude product was purified by silica gel chromatography and eluted with hexane-ethyl acetate (3:7) containing acetic acid (1%), followed by recrystallization from ethanol. Yield: 256 mg, 22.8%.

後処理

  1. additionwas added
  2. customCatalyst was then removed by filtration, and solvent
  3. customwas evaporated under reduced pressure

出典と根拠

ORDレコード
ord-a120ed118a774759b1fa0038c518c05e
出典データセット
uspto-grants-2008_01
特許番号
US07323496B2

反応ノート

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