Sodium borohydride → HCID 178486576, Verbindung

HRID 1017748

Reaktionsgleichung

Reaktionsgleichung von HRID 1017748
[NH:1]1[CH:5]=[C:4]([CH:6]2[C:14]3[C:9](=[C:10]([CH3:18])[C:11]([CH3:17])=[C:12]([O:15][CH3:16])[CH:13]=3)[C:8](=[O:19])[CH2:7]2)[N:3]=[CH:2]1.[BH4-].[Na+]>C(O)C>[NH:1]1[CH:5]=[C:4]([CH:6]2[C:14]3[C:9](=[C:10]([CH3:18])[C:11]([CH3:17])=[C:12]([O:15][CH3:16])[CH:13]=3)[CH:8]([OH:19])[CH2:7]2)[N:3]=[CH:2]1

Komponenten

4

Edukt 2

HCID 4311764Sodium borohydrideHCID 178486575HCID 178486575, Verbindung

Produkt 1

HCID 178486576HCID 178486576, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Reaktionsbedingungen

Temperatur
37.5 °C

Versuchsvorschrift

3-(1H-Imidazol-4-yl)-5-methoxy-6,7-dimethylindan-1-one (0.53 g) is dissolved in ethanol (30 ml) and 0.3 g of sodium borohydride is added. The mixture is stirred at 35-40° C. for 7 hours. About 20 ml of ethanol is then distilled off and 30 ml of water is added. The solution is extracted with ethyl acetate. The combined ethyl acetate extracts are washed with water, dried with sodium sulfate, and evaporated under reduced pressure. The product is the mixture of cis- and trans-isomers (about 85:15). Crystallization of the product from ethyl acetate gives a cis-isomer, m.p. 184-189° C.

Aufarbeitung

  1. distillationAbout 20 ml of ethanol is then distilled off
  2. addition30 ml of water is added
  3. extractionThe solution is extracted with ethyl acetate
  4. washThe combined ethyl acetate extracts are washed with water
  5. dry with materialdried with sodium sulfate
  6. customevaporated under reduced pressure
  7. additionthe mixture of cis- and trans-isomers (about 85:15)
  8. customCrystallization of the product from ethyl acetate
  9. customgives a cis-isomer, m.p. 184-189° C.

Quellen und Nachweise

ORD-Eintrag
ord-a20012a5791f4dbea2b078f9a4c0951c
Quelldatensatz
uspto-grants-2002_11
Patentnummer
US06479530B2

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