Trifluoroacetic acid → Diethyl (5-benzoylpyrrol-2-yl)methane-dicarboxylate

HRID 1090817

反応式

HRID 1090817 の反応式
[C:1]([C:9]1[NH:13][C:12]([C:14](OC(=O)C)([C:20]([O:22][CH2:23][CH3:24])=[O:21])[C:15]([O:17][CH2:18][CH3:19])=[O:16])=[CH:11][CH:10]=1)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C([SiH](CC)CC)C.FC(F)(F)C(O)=O>C(Cl)Cl>[C:1]([C:9]1[NH:13][C:12]([CH:14]([C:20]([O:22][CH2:23][CH3:24])=[O:21])[C:15]([O:17][CH2:18][CH3:19])=[O:16])=[CH:11][CH:10]=1)(=[O:8])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

参加物

5

反応物 3

HCID 6422Trifluoroacetic acid2 回HCID 12052Triethylsilane2 回HCID 54151482Diethyl (5-benzoylpyrrol-2-yl)-acetoxymethanedicarboxylate

生成物 1

HCID 9949366Diethyl (5-benzoylpyrrol-2-yl)methane-dicarboxylate収率 50%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

反応条件

温度
40 °C

実験手順

To a solution of diethyl (5-benzoylpyrrol-2-yl)-acetoxymethanedicarboxylate (142 mg, 0.367 mmol) and triethylsilane (102 mg, 0.440 mmol) in methylene chloride (10 mL) was added trifluoroacetic acid (84 mg, 0.734 mmol). The reaction mixture was stirred at 40° C. for 24 hours. Additional triethyl silane (51 mg, 0.220 mmol) and trifluoroacetic acid (84 mg, 0.734 mmol) was added. The reaction mixture was stirred at 40° C. for an additional 24 hours. The mixture was cooled to room temperature, washed with cold 10% aqueous sodium hydroxide and saturated aqueous sodium chloride, and concentrated under reduced pressure. The residue was purified by column chromatography on silica eluting with hexane/ethyl acetate (87:13) to provide 60 mg (50%) of diethyl (5-benzoylpyrrol-2-yl)methane-dicarboxylate.

後処理

  1. stirringThe reaction mixture was stirred at 40° C. for an additional 24 hours
  2. temperatureThe mixture was cooled to room temperature
  3. washwashed with cold 10% aqueous sodium hydroxide and saturated aqueous sodium chloride
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by column chromatography on silica eluting with hexane/ethyl acetate (87:13)

出典と根拠

ORDレコード
ord-45462bd281c8487caa0b0a8ec0a9d15f
出典データセット
uspto-grants-1992_01
特許番号
US05082950

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