Potassium Carbonate → Nonanoic acid, 9-hydroxy-, methyl ester

HRID 475704

Reaktionsgleichung

Reaktionsgleichung von HRID 475704
[CH3:1][O:2][C:3](=[O:14])[CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][C:11](O)=[O:12].B.CSC.C([O-])([O-])=O.[K+].[K+]>C1COCC1>[CH3:1][O:2][C:3](=[O:14])[CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][OH:12]

Komponenten

5

Edukt 3

HCID 11430Potassium CarbonateHCID 75009Monomethyl azelateHCID 12423031(Dimethyl sulfide)trihydroboron

Produkt 1

HCID 292983Nonanoic acid, 9-hydroxy-, methyl esterAusbeute 55 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel2×

Versuchsvorschrift

To a solution of nonanedioic acid monomethyl ester (4.80 g, 20 mmol) in THF (20 mL) at −20° C. was added a solution of borane-dimethylsulfide in THF (2.0 M, 10 mL) over 10 min. The resulting mixture was stirred for an additional 10 min, and then allowed to stir at room temperature overnight. Aqueous K2CO3 solution was added, and the product was extracted with ethyl ether (3×). The crude product was purified by flash column chromatography (hexane/EtOAc:2/1) to yield 9-hydroxy-nonanoic acid methyl ester 4-B (2.0 g, 55%).

Aufarbeitung

  1. stirringto stir at room temperature overnight
  2. extractionthe product was extracted with ethyl ether (3×)
  3. customThe crude product was purified by flash column chromatography (hexane/EtOAc:2/1)

Quellen und Nachweise

ORD-Eintrag
ord-f0b87447097d489f8d8290601e39f4e9
Quelldatensatz
uspto-grants-2014_01
Patentnummer
US08637648B1

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