Sodium Bicarbonate → HCID 58081223, Verbindung

HRID 928433Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 928433
[CH3:1][C:2]1[CH:11]=[C:10]2[C:5]([CH:6]=[C:7]([CH:12]=[O:13])[CH:8]=[N:9]2)=[CH:4][CH:3]=1.[Li+].[BH4-].C([O-])(O)=O.[Na+]>C1COCC1>[CH3:1][C:2]1[CH:11]=[C:10]2[C:5]([CH:6]=[C:7]([CH2:12][OH:13])[CH:8]=[N:9]2)=[CH:4][CH:3]=1

Komponenten

5

Edukt 3

HCID 516892Sodium BicarbonateHCID 4148881Lithium borohydrideHCID 128710747-Methylquinoline-3-carbaldehyde

Produkt 1

HCID 58081223HCID 58081223, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel2×

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

To a solution of 7-methyl-3-quinoline carboxaldehyde (200 mg, 1.168 mmol) in THF (4.5 ml) was added 2M LiBH4 solution in THF (2.337 ml, 4.67 mmol) at 0° C. Reaction mixture was stirred at 0° C. for 2 h, then slowly poured into NaHCO3 sat. solution and extracted twice with ethyl acetate. Organic layer was dried over sodium sulfate, filtered and evaporated to afford the crude material, which was purified by silica gel chromatography (cyclohexane/ethyl acetate form 100/0 to 0/100) to afford the title compound. HPLC (Method G) Rt=0.68 min, MS (Method V) [M+H]+=174.2.

Aufarbeitung

  1. customReaction mixture
  2. extractionextracted twice with ethyl acetate
  3. dry with materialOrganic layer was dried over sodium sulfate
  4. filtrationfiltered
  5. customevaporated
  6. customto afford the crude material, which
  7. customwas purified by silica gel chromatography (cyclohexane/ethyl acetate form 100/0 to 0/100)

Quellen und Nachweise

ORD-Eintrag
ord-a43f647e869149aaa23a05e18bf87b9d
Quelldatensatz
uspto-grants-2016_03
Patentnummer
US09290485B2

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