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

HRID 625730

Reaktionsgleichung

Reaktionsgleichung von HRID 625730
[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-4ec8fd7e5739410b8e0301f960ca1723
Quelldatensatz
uspto-grants-2016_04
Patentnummer
US09308272B2

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