Ethanol → 2-(6-Fluoroquinolin-2-yl)ethanol

HRID 920888

Reaktionsgleichung

Reaktionsgleichung von HRID 920888
[F:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[C:7]([CH3:12])[CH:6]=[CH:5]2.[OH-].[Na+].C=O.C[CH2:18][OH:19]>O>[F:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[C:7]([CH2:12][CH2:18][OH:19])[CH:6]=[CH:5]2

Komponenten

6

Edukt 4

HCID 702EthanolHCID 712FormaldehydeHCID 14798Sodium HydroxideHCID 707846-Fluoro-2-methylquinoline

Produkt 1

HCID 836745642-(6-Fluoroquinolin-2-yl)ethanolAusbeute 30,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Reaktionsbedingungen

Temperatur
85 °C

Versuchsvorschrift

6-Fluoro-2-methylquinoline (1.00 g, 6.20 mmol) and sodium hydroxide were each added sequentially to the mixture of HCHO in water. Then 2 mL of EtOH were added to the mixture. The resulting solution was stirred at about 85° C. overnight. The organic layer was extracted with EA (3×10 mL), collected and dried with anhydrous Na2SO4, filtered and concentrated to afford a pink oil. The crude material was purified by chromatography on silica-gel (eluent: PE/EA=6/1) and then further purified by combi-flash chromatography (NH4HCO3/H2O, MeOH/H2O=40%-60%) to give 360 mg of the title product (yield: 30.3%).

Aufarbeitung

  1. extractionThe organic layer was extracted with EA (3×10 mL)
  2. customcollected
  3. dry with materialdried with anhydrous Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customto afford a pink oil
  7. customThe crude material was purified by chromatography on silica-gel (eluent: PE/EA=6/1)
  8. customfurther purified by combi-flash chromatography (NH4HCO3/H2O, MeOH/H2O=40%-60%)

Quellen und Nachweise

ORD-Eintrag
ord-9d5a1de7af2a4998b6cc81a8e44567c4
Quelldatensatz
uspto-grants-2016_03
Patentnummer
US09273068B2

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