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

HRID 332871ノート

反応式

HRID 332871 の反応式
[OH:1][C:2]1[CH:7]=[CH:6][C:5](/[CH:8]=[CH:9]/[C:10]([O:12][CH3:13])=[O:11])=[CH:4][CH:3]=1.[H-].[Na+].Br[C:17]1[C:18]2[CH:34]=[CH:33][C:32]([O:35][CH3:36])=[CH:31][C:19]=2[S:20](=[O:30])[C:21]=1[C:22]1[CH:27]=[CH:26][C:25]([O:28][CH3:29])=[CH:24][CH:23]=1>CN(C=O)C>[CH3:36][O:35][C:32]1[CH:33]=[CH:34][C:18]2[C:17]([O:1][C:2]3[CH:3]=[CH:4][C:5](/[CH:8]=[CH:9]/[C:10]([O:12][CH3:13])=[O:11])=[CH:6][CH:7]=3)=[C:21]([C:22]3[CH:27]=[CH:26][C:25]([O:28][CH3:29])=[CH:24][CH:23]=3)[S:20](=[O:30])[C:19]=2[CH:31]=1

参加物

5

反応物 3

HCID 24758Sodium hydrideHCID 5319562Methyl-P-CoumarateHCID 159594683-Bromo-6-methoxy-2-(4-methoxyphenyl)benzothiophene 1-oxide

生成物 1

HCID 86730656(E)-methyl 3-(4-((6-methoxy-2-(4-methoxyphenyl)-1-oxidobenzo[b]thiophen-3-yl)oxy)phenyl)acrylate収率 97.6%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
80 °C

実験手順

To a solution of (E)-methyl 3-(4-hydroxyphenyl)acrylate (190 mg, 1.07 mmol) in DMF (5 mL) was added sodium hydride (60% suspension in oil, 42.7 mg, 1.07 mmol). The resulting mixture was allowed to stir for 10 min at room temperature after which 3-bromo-6-methoxy-2-(4-methoxyphenyl)benzo[b]thiophene 1-oxide (300 mg, 0.82 mmol) was added, as a solid. The reaction was heated to 80° C. for 18 h and upon completion was cooled to room temperature, quenched with water and diluted with DCM. The organic phase was collected (phase separator) and concentrated in vacuo to afford the crude product which was purified by column chromatography (SiO2, 0-80% EtOAc/Heptane) to afford (E)-methyl 3-(4-((6-methoxy-2-(4-methoxyphenyl)-1-oxidobenzo[b]thiophen-3-yl)oxy)phenyl)acrylate (370 mg, 0.80 mmol, 97% yield) as a yellow solid. 1H NMR (400 MHz, CDCl3) δ ppm=7.75 (d, J=9.09 Hz, 2H), 7.65 (d, J=15.66 Hz, 1H), 7.54 (d, J=2.02 Hz, 1H), 7.43-7.52 (m, J=9.09 Hz, 2H), 7.07-7.16 (m, J=8.59 Hz, 2H), 6.98-7.07 (m, 1H), 6.93 (d, J=9.09 Hz, 3H), 6.35 (d, J=16.17 Hz, 1H), 3.91 (s, 3H), 3.82 (d, J=1.52 Hz, 6H). LC/MS (m/z, MH+): 463.4.

後処理

  1. additionwas added, as a solid
  2. temperaturewas cooled to room temperature
  3. customquenched with water
  4. additiondiluted with DCM
  5. customThe organic phase was collected (phase separator)
  6. concentrationconcentrated in vacuo
  7. customto afford the crude product which
  8. customwas purified by column chromatography (SiO2, 0-80% EtOAc/Heptane)

出典と根拠

ORDレコード
ord-8ee016605d51454da8df4b074b3932a7
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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