Hydrochloric Acid → 6-cyano-2,2-dimethyl-4-(1,2-dihydro-2-oxo-4-hydroxymethyl-1-pyridinyl)-2H-benzo[b]pyran

HRID 487630Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 487630
[C:1]([C:3]1[CH:30]=[CH:29][C:6]2[O:7][C:8]([CH3:28])([CH3:27])[CH:9]=[C:10]([N:11]3[CH:16]=[CH:15][C:14]([CH2:17][O:18][Si](C(C)(C)C)(C)C)=[CH:13][C:12]3=[O:26])[C:5]=2[CH:4]=1)#[N:2].Cl>CO.O1CCOCC1>[C:1]([C:3]1[CH:30]=[CH:29][C:6]2[O:7][C:8]([CH3:27])([CH3:28])[CH:9]=[C:10]([N:11]3[CH:16]=[CH:15][C:14]([CH2:17][OH:18])=[CH:13][C:12]3=[O:26])[C:5]=2[CH:4]=1)#[N:2]

Komponenten

5

Edukt 2

HCID 313Hydrochloric AcidHCID 217469076-cyano-2,2-dimethyl-4-(1,2-dihydro-2-oxo-4-t-butyldimethylsilyloxymethyl-1-pyridinyl)-2H-benzo[b]pyran

Produkt 1

HCID 190925956-cyano-2,2-dimethyl-4-(1,2-dihydro-2-oxo-4-hydroxymethyl-1-pyridinyl)-2H-benzo[b]pyranAusbeute 100,2 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 887MethanolLösungsmittelHCID 312751,4-DioxaneLösungsmittel

Versuchsvorschrift

In 10.5 ml of methanol, is dissolved 1.04 g of 6-cyano-2,2-dimethyl-4-(1,2-dihydro-2-oxo-4-t-butyldimethylsilyloxymethyl-1-pyridinyl)-2H-benzo[b]pyran obtained in Example 8. Then, 2.59 ml of a 4N hydrochloric acid in dioxane is added to the solution at 0° C., and the resulting mixture is reacted at room temperature for 2 hours. The reaction mixture is concentrated under reduced pressure, the residue is mixed with ethyl acetate and water and the product is extracted into the ethyl acetate. The organic layer is washed with saturated aqueou solution of sodium chloride and dried over anhydrous sodium sulfate. The inorganic matter is filtered off, and the filtrate is concentrated under reduced pressure. The residue is purified by silica gel column chromatography using 1/20 mixture of methanol/methylene chloride as a developing solvent to obtain 0.76 g of 6-cyano-2,2-dimethyl-4-(1,2-dihydro-2-oxo-4-hydroxymethyl-1-pyridinyl)-2H-benzo[b]pyran.

Aufarbeitung

  1. customthe resulting mixture is reacted at room temperature for 2 hours
  2. concentrationThe reaction mixture is concentrated under reduced pressure
  3. additionthe residue is mixed with ethyl acetate and water
  4. extractionthe product is extracted into the ethyl acetate
  5. washThe organic layer is washed with saturated aqueou solution of sodium chloride
  6. dry with materialdried over anhydrous sodium sulfate
  7. filtrationThe inorganic matter is filtered off
  8. concentrationthe filtrate is concentrated under reduced pressure
  9. customThe residue is purified by silica gel column chromatography
  10. addition1/20 mixture of methanol/methylene chloride as a developing solvent

Quellen und Nachweise

ORD-Eintrag
ord-50fefa3699dd49d299f4567d1e2a52ad
Quelldatensatz
uspto-grants-1994_03
Patentnummer
US05296492

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