Water → Methyl-4-(4-oxo-4H-chromen-3-ylmethyl)-benzoate

HRID 736489

反応式

HRID 736489 の反応式
O.[O:2]=[C:3]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[O:6][CH2:5][C:4]1=[CH:13][C:14]1[CH:23]=[CH:22][C:17]([C:18]([O:20][CH3:21])=[O:19])=[CH:16][CH:15]=1>CCO.C(OCC)(=O)C>[CH3:21][O:20][C:18](=[O:19])[C:17]1[CH:22]=[CH:23][C:14]([CH2:13][C:4]2[C:3](=[O:2])[C:12]3[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=3)[O:6][CH:5]=2)=[CH:15][CH:16]=1

参加物

5

反応物 2

HCID 962WaterHCID 4240115Methyl 4-(4-oxo-chroman-3-ylidenemethyl)-benzoate

生成物 1

HCID 22478819Methyl-4-(4-oxo-4H-chromen-3-ylmethyl)-benzoate収率 59%

試薬・触媒・溶媒 2

HCID 702Ethanol溶媒HCID 8857Ethyl Acetate溶媒

反応条件

温度
70 °C

実験手順

Water (0.2 ml) and RhCl3.H2O (7 mg, 0.034 mmol) was added to a suspension of compound 260 (200 mg, 0.680 mmol) in EtOH (2 ml) and CDCl3 (2 ml). The reaction mixture was stirred 16 h at 70° C. The reaction mixture was cooled down and diluted in ethyl acetate, washed with brine, dried over anhydrous MgSO4, filtered and concentrated. The crude residue was then purified by flash chromatography on silica gel (0.5-1% MeOH/CH2Cl2)to afford the title compound 261 (118 mg, 59%) as a white solid. 1H NMR: (DMSO) δ (ppm): 8.45 (s, 1H), 8.03 (dd, J=7.9, 1.8 Hz, 1H), 7.87 (d, J=8.4 Hz, 2H), 7.83-7.77(m, 1H), 7.65 (d, J=8.3 Hz, 1H), 7.50-7.43 (m3, 1H), 3.82 (s, 3H), 3.80 (s, 2H).

後処理

  1. temperatureThe reaction mixture was cooled down
  2. washwashed with brine
  3. dry with materialdried over anhydrous MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe crude residue was then purified by flash chromatography on silica gel (0.5-1% MeOH/CH2Cl2)

出典と根拠

ORDレコード
ord-de7c46c57cc946d98a53df9edb6631ff
出典データセット
uspto-grants-2009_09
特許番号
US07595343B2

関連ノート

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