Methanol → Pyrazolo[5,1-b]oxazole-6-methanol, 2,3-dihydro-

HRID 2216618Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2216618
C([O:3][C:4]([C:6]1[CH:13]=[C:9]2[O:10][CH2:11][CH2:12][N:8]2[N:7]=1)=O)C.[BH4-].[Li+].CO>C1COCC1>[O:10]1[CH2:11][CH2:12][N:8]2[N:7]=[C:6]([CH2:4][OH:3])[CH:13]=[C:9]12

Komponenten

5

Edukt 3

HCID 887MethanolHCID 4148881Lithium borohydrideHCID 69588863Ethyl 2,3-dihydropyrazolo[5,1-b]oxazole-6-carboxylate

Produkt 1

HCID 21941355Pyrazolo[5,1-b]oxazole-6-methanol, 2,3-dihydro-Ausbeute 65 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
40 °C

Versuchsvorschrift

To the stirred solution of ethyl2,3-dihydropyrazolo[5,1-b][1,3]oxazole-6-carboxylate (5.47 g, 35 mmol) of in 100 ml of THF was added 1.05 g of lithium borohydride and 1.54 g of methanol. The solution was heated at 40° C. for 2.5 hour. The reaction was quenched by 1N HCl, and adjusted to pH 1.3 and stirred at room temperature for 1 hour. The reaction mixture was adjusted pH to 8 with k2CO3. The reaction mixture was extracted with ethyl acetate. The organic layer was dried over MgSO4, and concentrated to an oil and column chromatographyed to give 2.68 g of the desired product (65%).

Aufarbeitung

  1. customThe reaction was quenched by 1N HCl
  2. extractionThe reaction mixture was extracted with ethyl acetate
  3. dry with materialThe organic layer was dried over MgSO4
  4. concentrationconcentrated to an oil and column

Quellen und Nachweise

ORD-Eintrag
ord-f2376497c33d49979401aa8f1efedffb
Quelldatensatz
uspto-grants-2006_09
Patentnummer
US07112582B2

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