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Tetrahydrofuran → Methyl(4-cyclopropyl-6-hydroxy-1-benzothiophen-3-yl)acetate

HRID 591507
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HRID 591507 반응식
[CH3:1][O:2][C:3](=[O:28])[CH2:4][C:5]1[C:9]2[C:10]([CH:25]3[CH2:27][CH2:26]3)=[CH:11][C:12]([O:14][Si](C(C)C)(C(C)C)C(C)C)=[CH:13][C:8]=2[S:7][CH:6]=1.C1COCC1.CCCC[N+](CCCC)(CCCC)CCCC.[F-]>O>[CH3:1][O:2][C:3](=[O:28])[CH2:4][C:5]1[C:9]2[C:10]([CH:25]3[CH2:27][CH2:26]3)=[CH:11][C:12]([OH:14])=[CH:13][C:8]=2[S:7][CH:6]=1
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참가 물질

5

반응물 3

HCID 8028TetrahydrofuranHCID 2724141Tetrabutylammonium FluorideHCID 131734522Methyl(4-cyclopropyl-6-((triisopropylsilyl)oxy)-1-benzothiophen-3-yl)acetate

생성물 1

HCID 131734523Methyl(4-cyclopropyl-6-hydroxy-1-benzothiophen-3-yl)acetate수율 86.2%

시약·촉매·용매 1

HCID 962Water용매

실험 절차

To a mixture of methyl(4-cyclopropyl-6-((triisopropylsilyl)oxy)-1-benzothiophen-3-yl)acetate (372 mg) and THF (2 mL) was added TBAF (1M in THF, 1.333 mL) at room temperature. The mixture was stirred at room temperature for 1 h. The mixture was poured into water at room temperature and extracted with EtOAc. The organic layer was separated, washed with brine, dried over MgSO4 and concentrated in vacuo. The residue was purified by silica gel column chromatography (EtOAc/hexane) to give the title compound (201 mg).

후처리

  1. extractionextracted with EtOAc
  2. customThe organic layer was separated
  3. washwashed with brine
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by silica gel column chromatography (EtOAc/hexane)

출처 및 근거

ORD 기록
ord-318f2eea7f5b440bb2f7ca5234f14ab0
출처 데이터셋
uspto-grants-2016_01
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09238639B2

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