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3,4-dihydro-2H-pyran → Ethyl 6-(tert-butyldiphenylsilyloxy)-1-(tetrahydro-2H-pyran-2-yl)indazole-3-carboxylate

HRID 1873953
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1873953
[CH2:1]([O:3][C:4]([C:6]1[C:14]2[C:9](=[CH:10][C:11]([O:15][Si:16]([C:29]([CH3:32])([CH3:31])[CH3:30])([C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)[C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)=[CH:12][CH:13]=2)[NH:8][N:7]=1)=[O:5])[CH3:2].[O:33]1[CH:38]=[CH:37][CH2:36][CH2:35][CH2:34]1.O.C1(C)C(S(O)(=O)=O)=CC=CC=1.C(=O)([O-])O.[Na+]>C1(C)C=CC=CC=1>[CH2:1]([O:3][C:4]([C:6]1[C:14]2[C:9](=[CH:10][C:11]([O:15][Si:16]([C:29]([CH3:31])([CH3:30])[CH3:32])([C:23]3[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=3)[C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)=[CH:12][CH:13]=2)[N:8]([CH:34]2[CH2:35][CH2:36][CH2:37][CH2:38][O:33]2)[N:7]=1)=[O:5])[CH3:2]
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 4

HCID 80803,4-dihydro-2H-pyranHCID 516892Sodium BicarbonateHCID 124969952-Methylbenzenesulfonic acid hydrateHCID 59370747Ethyl6-tert-butyldiphenylsilyloxyindazole-3-carboxylate

Produkt 1

HCID 59370763Ethyl 6-(tert-butyldiphenylsilyloxy)-1-(tetrahydro-2H-pyran-2-yl)indazole-3-carboxylate

Reagenzien, Katalysatoren, Lösungsmittel

1
HCID 1140TolueneLösungsmittel

Reaktionsbedingungen

Temperatur
60 °C

Versuchsvorschrift

Ethyl6-tert-butyldiphenylsilyloxyindazole-3-carboxylate (1.461 g) which can be prepared according to the method described in Reference example 18, etc. was dissolved in toluene (16.5 mL; manufactured by Wako Pure Chemical Industries, Ltd.), added with 3,4-dihydro-2H-pyran (0.6 mL; manufactured by Tokyo Chemical Industry, Co., Ltd.) and toluene sulfonic acid-monohydrate (0.1293 g), followed by stirring overnight at 60° C. under nitrogen atmosphere. The reaction solution was poured to a saturated aqueous solution of sodium hydrogen carbonate and extracted once with ethyl acetate. The organic layer was washed twice with water and once 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=96:4→75:25) to obtain the title compound (1.334 g).

Aufarbeitung

  1. extractionextracted once with ethyl acetate
  2. washThe organic layer was washed twice with water and once with brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customAfter the solvent was evaporated under reduced pressure
  5. customthe residue was purified by column chromatography “COLUMN-A”

Quellen und Nachweise

ORD-Eintrag
ord-3e8e9e2803e84802b3d953943386a3b1
Quelldatensatz
uspto-grants-2012_11
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08304443B2

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