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

HRID 332871노트

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HRID 332871 반응식
[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

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

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온도
80 °C

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-8ee016605d51454da8df4b074b3932a7
출처 데이터셋
uspto-grants-2014_11
특허 번호
US08877801B2

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