Nitric Acid → 2-(2-Benzyloxy-5-nitrophenyl)-2-methylpropionic acid methyl ester

HRID 1861967ノート

反応式

HRID 1861967 の反応式
S(=O)(=O)(O)O.[N+:6]([O-:9])(O)=[O:7].[CH3:10][O:11][C:12](=[O:30])[C:13]([C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=1[O:22][CH2:23][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)([CH3:15])[CH3:14].C(OCC)(=O)C>C(O)(=O)C>[CH3:10][O:11][C:12](=[O:30])[C:13]([C:16]1[CH:21]=[C:20]([N+:6]([O-:9])=[O:7])[CH:19]=[CH:18][C:17]=1[O:22][CH2:23][C:24]1[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=1)([CH3:15])[CH3:14]

参加物

6

反応物 4

HCID 944Nitric AcidHCID 1118Sulfuric AcidHCID 8857Ethyl AcetateHCID 229809602-(2-Benzyloxyphenyl)-2-methylpropionic acid methyl ester

生成物 1

HCID 229809592-(2-Benzyloxy-5-nitrophenyl)-2-methylpropionic acid methyl ester収率 46%

試薬・触媒・溶媒 1

HCID 176Acetic Acid溶媒

反応条件

温度
45 °C

実験手順

To a mixture of sulfuric acid (0.27 ml) and nitric acid (0.34 ml), a solution of the compound (1.0 g) obtained in Example 561 in acetic acid (30 ml) was added dropwise at 5° C. The reaction mixture was stirred at 45° C. for 4 h, poured into ice cold water and ethyl acetate was added to the mixture. The organic layer was washed with a saturated aqueous sodium bicarbonate solution and a saturated aqueous sodium chloride solution, dried with anhydrous sodium sulfate and the solvent was distilled off under reduced pressure. The resulting residue was purified by silica gel column chromatography (eluent, n-hexane:ethyl acetate=9:1) to give 530 mg of the titled compound (yield, 46%).

後処理

  1. additionwas added to the mixture
  2. washThe organic layer was washed with a saturated aqueous sodium bicarbonate solution
  3. dry with materiala saturated aqueous sodium chloride solution, dried with anhydrous sodium sulfate
  4. distillationthe solvent was distilled off under reduced pressure
  5. customThe resulting residue was purified by silica gel column chromatography (eluent, n-hexane:ethyl acetate=9:1)

出典と根拠

ORDレコード
ord-5268074992f94beda50fb17d68ce791d
出典データセット
uspto-grants-2003_03
特許番号
US06534546B1

反応ノート

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