Sodium Hydroxide → HCID 21186666, Verbindung

HRID 1384277Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1384277
O[CH:2]1[C:8]2=[N:9][C:10]([CH3:18])=[C:11]([C:13]([O:15][CH2:16][CH3:17])=[O:14])[CH:12]=[C:7]2[CH2:6][CH2:5][CH2:4][CH2:3]1.S(Cl)([Cl:21])=O.[OH-].[Na+]>C(Cl)(Cl)Cl>[Cl:21][CH:2]1[C:8]2=[N:9][C:10]([CH3:18])=[C:11]([C:13]([O:15][CH2:16][CH3:17])=[O:14])[CH:12]=[C:7]2[CH2:6][CH2:5][CH2:4][CH2:3]1

Komponenten

5

Edukt 3

HCID 14798Sodium HydroxideHCID 24386Thionyl ChlorideHCID 21186673HCID 21186673, Verbindung

Produkt 1

HCID 21186666HCID 21186666, VerbindungAusbeute 79,8 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6212ChloroformLösungsmittel

Versuchsvorschrift

Ethyl 9-hydroxy-2-methyl-6,7,8,9-tetrahydro-5H-cyclohepta[b]pyridine-3-carboxylate (3.92 g, 15.7mmol) was dissolved in chloroform (12.0 ml) to which was subsequently added dropwise thionyl chloride (4.4 ml) at −11° C. This was stirred at room temperature for 21 hours, and the reaction solution was poured into ice water, adjusted to pH 8 with 2 N sodium hydroxide aqueous solution and then extracted with chloroform. The thus obtained organic layer was washed with water and saturated brine in that order and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure and the resulting residue was purified by a silica gel column chromatography (ether:hexane=1:2) to obtain the title compound (3.35 g, 79.8%) as pale yellow oil.

Aufarbeitung

  1. extractionextracted with chloroform
  2. washThe thus obtained organic layer was washed with water and saturated brine in that order
  3. dry with materialdried over anhydrous sodium sulfate
  4. customThe solvent was evaporated under reduced pressure
  5. customthe resulting residue was purified by a silica gel column chromatography (ether:hexane=1:2)

Quellen und Nachweise

ORD-Eintrag
ord-fdc0d58e647f450fbb1a4f76666256c3
Quelldatensatz
uspto-grants-2001_07
Patentnummer
US06258829B1

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