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

HRID 1158914Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1158914
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

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 chromatographed to give 2.68 g of the desired product (65%).

Aufarbeitung

  1. temperatureThe solution was heated at 40 C for 2.5 hour
  2. customThe reaction was quenched by 1N HCl
  3. extractionThe reaction mixture was extracted with ethyl acetate
  4. dry with materialThe organic layer was dried over MgSO4
  5. concentrationconcentrated to an oil and column
  6. customchromatographed

Quellen und Nachweise

ORD-Eintrag
ord-f4c0870fad634c84aa98d53ae9e89b85
Quelldatensatz
uspto-grants-2010_10
Patentnummer
US07812014B2

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