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Ethyl Acetate → Ethyl 6-hydroxy-1-(tetrahydro-2H-pyran-2-yl)indazole-3-carboxylate

HRID 1873954
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HRID 1873954 반응식
[CH2:1]([O:3][C:4]([C:6]1[C:14]2[C:9](=[CH:10][C:11]([O:15][Si](C(C)(C)C)(C3C=CC=CC=3)C3C=CC=CC=3)=[CH:12][CH:13]=2)[N:8]([CH:33]2[CH2:38][CH2:37][CH2:36][CH2:35][O:34]2)[N:7]=1)=[O:5])[CH3:2].CCCC[N+](CCCC)(CCCC)CCCC.[F-].C1COCC1.C(OCC)(=O)C>C1COCC1>[CH2:1]([O:3][C:4]([C:6]1[C:14]2[C:9](=[CH:10][C:11]([OH:15])=[CH:12][CH:13]=2)[N:8]([CH:33]2[CH2:38][CH2:37][CH2:36][CH2:35][O:34]2)[N:7]=1)=[O:5])[CH3:2]
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참가 물질

5

반응물 3

HCID 8857Ethyl AcetateHCID 11078149TBAF tetrahydrofuranHCID 59370763Ethyl 6-(tert-butyldiphenylsilyloxy)-1-(tetrahydro-2H-pyran-2-yl)indazole-3-carboxylate

생성물 1

HCID 136205191Ethyl 6-hydroxy-1-(tetrahydro-2H-pyran-2-yl)indazole-3-carboxylate수율 92.5%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

Ethyl6-(tert-butyldiphenylsilyloxy)-1-(tetrahydro-2H-pyran-2-yl)-indazole-3-carboxylate (1.299 g) which can be prepared according to the method described in Reference example 19, etc. was dissolved in dehydrated THF (12.3 mL; manufactured by Kanto Chemical Co., Inc.), added with 1 mol/L-TBAF-THF solution (3.69 mL; manufactured by Sigma-Aldrich Co.), followed by stirring for 2 hours at room temperature under nitrogen atmosphere. The reaction solution was added with ethyl acetate, washed three times with brine, and dried over anhydrous magnesium sulfate. After the solvent was evaporated under reduced pressure, the residue was purified by column chromatography “COLUMN-A”; n-hexane:ethyl acetate=100:0→81:19) to obtain the title compound (0.660 g).

후처리

  1. washwashed three times with brine
  2. dry with materialdried over anhydrous magnesium sulfate
  3. customAfter the solvent was evaporated under reduced pressure
  4. customthe residue was purified by column chromatography “COLUMN-A”

출처 및 근거

ORD 기록
ord-1150ea9291c64d129197b6dd585410a9
출처 데이터셋
uspto-grants-2012_11
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08304443B2

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