Diethyl Ether → (4,6-Dihydropyrazolo[1,5-c]thiazol-2-yl)methanol

HRID 1158909Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1158909
[Li+].[BH4-].CCOCC.C([O:10][C:11]([C:13]1[CH:20]=[C:19]2[N:15]([CH2:16][S:17][CH2:18]2)[N:14]=1)=O)C>CO>[N:14]1[N:15]2[C:19]([CH2:18][S:17][CH2:16]2)=[CH:20][C:13]=1[CH2:11][OH:10]

Komponenten

5

Edukt 3

HCID 3283Diethyl EtherHCID 4148881Lithium borohydrideHCID 21057705Ethyl 4H,6H-pyrazolo[1,5-c]thiazole-2-carboxylate

Produkt 1

HCID 21941435(4,6-Dihydropyrazolo[1,5-c]thiazol-2-yl)methanol

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

LiBH4 (cont. 90%) (459 mg) was added to the ether (126 mL) solution of 4H-5-thia-1,6a-diazapentalen-2-carboxylic acid ethylester (2.5 g) and MeOH (0.77 mL) under a nitrogen atmosphere at room temperature, then refluxed for 1.5 h. The mixture was quenched with 1 mol/L HCl (25 mL) and stirred for 1 h at room temperature. The mixture was neutralized by saturated sodium hydrogen carbonate solution and separated. The aqueous layer was extracted with dichloromethane (10×25 mL). The organic layer was dried (MgSO4) and filtered. The filtrate was concentrated under reduced pressure. The residue was applied to silica gel column chromatography, then the column was eluted with AcOEt. The titled compound was obtained as a pale yellow solid (1.7 g, 87.9%).

Aufarbeitung

  1. temperaturerefluxed for 1.5 h
  2. customThe mixture was quenched with 1 mol/L HCl (25 mL)
  3. customseparated
  4. extractionThe aqueous layer was extracted with dichloromethane (10×25 mL)
  5. dry with materialThe organic layer was dried (MgSO4)
  6. filtrationfiltered
  7. concentrationThe filtrate was concentrated under reduced pressure
  8. washthe column was eluted with AcOEt

Quellen und Nachweise

ORD-Eintrag
ord-b389bf33e0d7446ea46033ced80086c9
Quelldatensatz
uspto-grants-2010_10
Patentnummer
US07812014B2

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