Methanol → Methyl 2-allyloctanoate

HRID 1180695Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1180695
COC(N([C@@H](C1C=CC=CC=1)C)C(=O)[CH:7]([CH2:14][CH:15]=[CH2:16])[CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH3:13])=O.[CH3:26][O-:27].[Na+].[CH3:29][OH:30]>>[CH2:11]([CH:10]([CH2:9][CH2:8][CH2:7][CH2:14][CH2:15][CH3:16])[C:26]([O:30][CH3:29])=[O:27])[CH:12]=[CH2:13]

Komponenten

4

Edukt 3

HCID 887MethanolHCID 10942334Sodium MethoxideHCID 69502051N-methyloxycarbonyl-N-(2-allyloctanoyl)-1-(R)-phenylethylamine

Produkt 1

HCID 23117480Methyl 2-allyloctanoateAusbeute 51 %

Versuchsvorschrift

A solution of 0.345 g (1.0 mmol) of N-methyloxycarbonyl-N-(2-allyloctanoyl)-1-(R)-phenylethylamine in 5 ml of methanol was cooled to 0° C., 0.386 g (2.0 mmol) of NaOMe (28% solution in methanol) was added, and the mixture was stirred for 22 hours. The reaction was terminated by addition of 2 ml of 1 N hydrochloric acid, and the product was extracted with ethyl acetate. The extract was dried over anhydrous sodium sulfate, the solvent was distilled off, and the residue was isolated/purified on a silica gel column to give 0.10 g (51%) of the title compound. N-(2-Allyloctanoyl)-(R)-1-phenylethylamine was formed as a byproduct in 45% yield.

Aufarbeitung

  1. customThe reaction was terminated by addition of 2 ml of 1 N hydrochloric acid
  2. extractionthe product was extracted with ethyl acetate
  3. dry with materialThe extract was dried over anhydrous sodium sulfate
  4. distillationthe solvent was distilled off
  5. customthe residue was isolated/purified on a silica gel column

Quellen und Nachweise

ORD-Eintrag
ord-ccda876f51db4a96885311fbfdbb1489
Quelldatensatz
uspto-grants-2007_10
Patentnummer
US07282605B2

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