Methyl iodide → Heptanoic acid, 6-oxo-, methyl ester

HRID 628940Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 628940
N12CCCN=C1CCCC[CH2:2]2.[O:12]=[C:13]([CH3:21])[CH2:14][CH2:15][CH2:16][CH2:17][C:18]([OH:20])=[O:19].IC>CC(C)=O>[O:12]=[C:13]([CH3:21])[CH2:14][CH2:15][CH2:16][CH2:17][C:18]([O:20][CH3:2])=[O:19]

Komponenten

5

Edukt 3

HCID 6328Methyl iodideHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 988106-Oxoheptanoic acid

Produkt 1

HCID 288022Heptanoic acid, 6-oxo-, methyl esterAusbeute 97,8 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 180AcetoneLösungsmittel

Versuchsvorschrift

1,8-Diazabicyclo[5.4.0]undec-7-ene (3.4 mL, 22.86 mmol) was added to a solution of 6-oxoheptanoic acid 23 (1.1 g, 7.63 mmol) in acetone (15 mL) at 23° C. After stirring for 15 min iodomethane (2.4 mL, 38.3 mmol) was added. The reaction was stirred for 1 h and then the solvent was removed in vacuo. The residue was purified by flash column chromatography (silica gel, 7:3 hex/EtOAc) to provide 1.18 g (95%) of the methyl ester 24 (see scheme 4).

Aufarbeitung

  1. additionwas added
  2. customthe solvent was removed in vacuo
  3. customThe residue was purified by flash column chromatography (silica gel, 7:3 hex/EtOAc)

Quellen und Nachweise

ORD-Eintrag
ord-07fb0fa9b4c94e7a93d0aed4974726bd
Quelldatensatz
uspto-grants-2016_04
Patentnummer
US09315486B2

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