Tetrabutylammonium Fluoride → (E)-isopropyl 3-(4-((6-hydroxy-2-(2-isopropylphenyl)benzo[b]thiophen-3-yl)oxy)phenyl)acrylate

HRID 632705노트

반응식

HRID 632705 반응식
[Si]([O:8][C:9]1[CH:10]=[CH:11][C:12]2[C:16]([O:17][C:18]3[CH:23]=[CH:22][C:21](/[CH:24]=[CH:25]/[C:26]([O:28][CH:29]([CH3:31])[CH3:30])=[O:27])=[CH:20][CH:19]=3)=[C:15]([C:32]3[CH:37]=[CH:36][CH:35]=[CH:34][C:33]=3[CH:38]([CH3:40])[CH3:39])[S:14][C:13]=2[CH:41]=1)(C(C)(C)C)(C)C.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>C1COCC1>[OH:8][C:9]1[CH:10]=[CH:11][C:12]2[C:16]([O:17][C:18]3[CH:19]=[CH:20][C:21](/[CH:24]=[CH:25]/[C:26]([O:28][CH:29]([CH3:31])[CH3:30])=[O:27])=[CH:22][CH:23]=3)=[C:15]([C:32]3[CH:37]=[CH:36][CH:35]=[CH:34][C:33]=3[CH:38]([CH3:40])[CH3:39])[S:14][C:13]=2[CH:41]=1

참가 물질

4

반응물 2

HCID 2724141Tetrabutylammonium FluorideHCID 131735441(E)-isopropyl 3-(4-((6-((tert-butyldimethylsilyl)oxy)-2-(2-isopropylphenyl)benzo[b]thiophen-3-yl)oxy)phenyl)acrylate

생성물 1

HCID 90372198(E)-isopropyl 3-(4-((6-hydroxy-2-(2-isopropylphenyl)benzo[b]thiophen-3-yl)oxy)phenyl)acrylate수율 49%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

To a solution of (E)-isopropyl 3-(4-((6-((tert-butyldimethylsilyl)oxy)-2-(2-isopropylphenyl)benzo[b]thiophen-3-yl)oxy)phenyl)acrylate (35 mg, 0.060 mmol) in THF (2.0 mL) at 0° C. was added tetra-n-butylammonium fluoride (1.0 M in THF, 0.089 mL, 0.089 mmol) dropwise, the reaction immediately turned bright yellow in color. Stirring was continued at 0° C. for 45 min after which the reaction was warmed to room temperature for 15 min and then quenched by addition of st. aq. NaHCO3. The aqueous layer was extracted with EtOAc (4×) and the combined organic layers were dried over anhydrous MgSO4, filtered and concentrated in vacuo. The resulting crude material was purified by column chromatography (SiO2, 0-20% EtOAc/Heptane) to afford (E)-isopropyl 3-(4-((6-hydroxy-2-(2-isopropylphenyl)benzo[b]thiophen-3-yl)oxy)phenyl)acrylate (14.0 mg, 0.029 mmol, 49% yield). 1H NMR (400 MHz, CD3OD) δ ppm=7.55 (d, J=16.0 Hz, 1H), 7.45 (d, J=8.8 Hz, 2H), 7.37-7.20 (m, 5H), 7.11 (td, J=7.6, 1.5 Hz, 1H), 6.89-6.81 (m, 3H), 6.32 (d, J=16.0 Hz, 11H), 5.05 (p, J=6.2 Hz, 1H), 3.23 (p, J=6.9 Hz, 1H), 1.28 (d, J=6.2 Hz, 6H), 1.16 (d, J=6.8 Hz, 6H). HRMS (m/z, MH+): 473.1774.

후처리

  1. customthe reaction immediately turned bright yellow in color
  2. customquenched by addition of st
  3. extractionThe aqueous layer was extracted with EtOAc (4×)
  4. dry with materialthe combined organic layers were dried over anhydrous MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe resulting crude material was purified by column chromatography (SiO2, 0-20% EtOAc/Heptane)

출처 및 근거

ORD 기록
ord-ae83859118484af09bc8a137f63e6e48
출처 데이터셋
uspto-grants-2016_04
특허 번호
US09321746B2

반응 노트

불러오는 중…