Ammonium Chloride → 6-cyano-2,2-dimethyl-4-{1,2-dihydro-2-oxo-4-(1-hydroxy)ethyl-1-pyridinyl}-2H-benzo[b]pyran

HRID 487642Notizen

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Reaktionsgleichung von HRID 487642
[C:1]([C:3]1[CH:23]=[CH:22][C:6]2[O:7][C:8]([CH3:21])([CH3:20])[CH:9]=[C:10]([N:11]3[CH:16]=[CH:15][C:14]([CH:17]=[O:18])=[CH:13][C:12]3=[O:19])[C:5]=2[CH:4]=1)#[N:2].[CH3:24][Mg]Br.[Cl-].[NH4+]>O1CCCC1>[C:1]([C:3]1[CH:23]=[CH:22][C:6]2[O:7][C:8]([CH3:20])([CH3:21])[CH:9]=[C:10]([N:11]3[CH:16]=[CH:15][C:14]([CH:17]([OH:18])[CH3:24])=[CH:13][C:12]3=[O:19])[C:5]=2[CH:4]=1)#[N:2]

Komponenten

5

Edukt 3

HCID 25517Ammonium ChlorideHCID 190925656-cyano-2,2-dimethyl-4-(1,2-dihydro-2-oxo-4-formyl-1-pyridinyl)-2H-benzo[b]pyranHCID 178418573HCID 178418573, Verbindung

Produkt 1

HCID 190926156-cyano-2,2-dimethyl-4-{1,2-dihydro-2-oxo-4-(1-hydroxy)ethyl-1-pyridinyl}-2H-benzo[b]pyran

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel2×

Versuchsvorschrift

In 4 ml of anhydrous tetrahydrofuran, is dissolved 355 mg of 6-cyano-2,2-dimethyl-4-(1,2-dihydro-2-oxo-4-formyl-1-pyridinyl)-2H-benzo[b]pyran obtained in Example 25. Then, 1.73 ml of 0.94 M solution of methylmagnesium bromide in tetrahydrofuran is added at 0° C. and reacted first at that temperature for 50 minutes and then at room temperature for 20 minutes. After stopping the reaction by adding a saturated aqueous solution of ammonium chloride, the reaction mixture is extracted with ethyl acetate, and the organic layer is washed with saturated aqueous 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 thus obtained is purified by silica gel column chromatography using 1/1 mixture of methylene chloride/ethyl acetate as a developing solvent. Thus, 281 mg of 6-cyano-2,2-dimethyl-4-{1,2-dihydro-2-oxo-4-(1-hydroxy)ethyl-1-pyridinyl}-2H-benzo[b]pyran is obtained.

Aufarbeitung

  1. customreacted first at that temperature for 50 minutes
  2. customthe reaction
  3. extractionthe reaction mixture is extracted with ethyl acetate
  4. washthe organic layer is washed with saturated aqueous solution of sodium chloride
  5. dry with materialdried over anhydrous sodium sulfate
  6. filtrationThe inorganic matter is filtered off
  7. concentrationthe filtrate is concentrated under reduced pressure
  8. customThe residue thus obtained
  9. customis purified by silica gel column chromatography
  10. addition1/1 mixture of methylene chloride/ethyl acetate as a developing solvent

Quellen und Nachweise

ORD-Eintrag
ord-5a31b60e5eb24caaa5f77d3aae1a56ea
Quelldatensatz
uspto-grants-1994_03
Patentnummer
US05296492

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