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

HRID 1873954
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1873954
[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]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

5

Edukt 3

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

Produkt 1

HCID 136205191Ethyl 6-hydroxy-1-(tetrahydro-2H-pyran-2-yl)indazole-3-carboxylateAusbeute 92,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028
Tetrahydrofuran
Lösungsmittel

Versuchsvorschrift

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).

Aufarbeitung

  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”

Quellen und Nachweise

ORD-Eintrag
ord-1150ea9291c64d129197b6dd585410a9
Quelldatensatz
uspto-grants-2012_11
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08304443B2

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