Sodium hydride → (E)-ethyl 3-(4-((6-methoxy-2-(4-methoxyphenyl)-1-oxidobenzo[b]thiophen-3-yl)oxy)phenyl)-2-methylacrylate

HRID 332872ノート

反応式

HRID 332872 の反応式
[OH:1][C:2]1[CH:7]=[CH:6][C:5](/[CH:8]=[C:9](\[CH3:15])/[C:10]([O:12][CH2:13][CH3:14])=[O:11])=[CH:4][CH:3]=1.[H-].[Na+].Br[C:19]1[C:20]2[CH:36]=[CH:35][C:34]([O:37][CH3:38])=[CH:33][C:21]=2[S:22](=[O:32])[C:23]=1[C:24]1[CH:29]=[CH:28][C:27]([O:30][CH3:31])=[CH:26][CH:25]=1>CN(C=O)C>[CH3:38][O:37][C:34]1[CH:35]=[CH:36][C:20]2[C:19]([O:1][C:2]3[CH:3]=[CH:4][C:5](/[CH:8]=[C:9](\[CH3:15])/[C:10]([O:12][CH2:13][CH3:14])=[O:11])=[CH:6][CH:7]=3)=[C:23]([C:24]3[CH:29]=[CH:28][C:27]([O:30][CH3:31])=[CH:26][CH:25]=3)[S:22](=[O:32])[C:21]=2[CH:33]=1

参加物

5

反応物 3

HCID 24758Sodium hydrideHCID 14920484(E)-ethyl 3-(4-hydroxyphenyl)-2-methylacrylateHCID 159594683-Bromo-6-methoxy-2-(4-methoxyphenyl)benzothiophene 1-oxide

生成物 1

HCID 86730657(E)-ethyl 3-(4-((6-methoxy-2-(4-methoxyphenyl)-1-oxidobenzo[b]thiophen-3-yl)oxy)phenyl)-2-methylacrylate収率 86%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒2 回

実験手順

To a solution of (E)-ethyl 3-(4-hydroxyphenyl)-2-methylacrylate (92 mg, 0.445 mmol) in DMF (2.0 mL) was added sodium hydride (60% suspension in oil, 17.79 mg, 0.445 mmol), the resulting mixture was allowed to stir for 30 min at room temperature. To the solution was added 3-bromo-6-methoxy-2-(4-methoxyphenyl)benzo[b]thiophene 1-oxide (125 mg, 0.342 mmol) as a suspension in DMF (2.0 mL). The reaction was heated to 80° C. for 15 h. Upon completion the reaction was cooled to room temperature, quenched with water and extracted with EtOAc. The combined organic layers were then washed with water, sat. aq. NaHCO3, brine and then collected (phase separator) and concentrated in vacuo to afford the crude product. The crude material was purified by column chromatography (SiO2, 0-70% EtOAc/Heptane) to afford (E)-ethyl 3-(4-((6-methoxy-2-(4-methoxyphenyl)-1-oxidobenzo[b]thiophen-3-yl)oxy)phenyl)-2-methylacrylate (144 mg, 0.294 mmol, 86% yield). LC/MS (m/z, MH+): 491.3

後処理

  1. temperatureThe reaction was heated to 80° C. for 15 h
  2. temperatureUpon completion the reaction was cooled to room temperature
  3. customquenched with water
  4. extractionextracted with EtOAc
  5. washThe combined organic layers were then washed with water, sat. aq. NaHCO3, brine
  6. customcollected (phase separator)
  7. concentrationconcentrated in vacuo
  8. customto afford the crude product
  9. customThe crude material was purified by column chromatography (SiO2, 0-70% EtOAc/Heptane)

出典と根拠

ORDレコード
ord-d88c4e5bab434aa0bb673b95abdfd030
出典データセット
uspto-grants-2014_11
特許番号
US08877801B2

反応ノート

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