Acetic Acid → Methyl 2-isocyano-2-(2-thienylmethyl)butyrate

HRID 1722734Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1722734
CC(C)([O-])C.[K+].[N+:7]([CH:9]([CH2:14][CH3:15])[C:10]([O:12][CH3:13])=[O:11])#[C-:8].Br[CH2:17][C:18]1[S:19][CH:20]=[CH:21][CH:22]=1.C(O)(=O)C>O1CCCC1>[N+:7]([C:9]([CH2:17][C:18]1[S:19][CH:20]=[CH:21][CH:22]=1)([CH2:14][CH3:15])[C:10]([O:12][CH3:13])=[O:11])#[C-:8]

Komponenten

6

Edukt 4

HCID 176Acetic AcidHCID 118299782-(Bromomethyl)thiopheneHCID 16754012Methyl 2-isocyanobutyrateHCID 23665647Potassium tert-butoxide

Produkt 1

HCID 20027427Methyl 2-isocyano-2-(2-thienylmethyl)butyrateAusbeute 88,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel2×

Reaktionsbedingungen

Temperatur
-30 °C

Versuchsvorschrift

A suspension of potassium tert.-butoxide (5.5 g) in tetrahydrofuran (50 ml) is cooled to -30° C., and a solution of methyl 2-isocyanobutyrate (5.5 g) in tetrahydrofuran (10 ml) is added dropwise to the suspension at -30° C. The mixture is stirred at the same temperature for 30 minutes and a solution of 2-bromomethylthiophene (6.9 g) in tetrahydrafuran (10 ml) is added dropwise to the mixture. The mixture is stirred at room temperature for 4 hours, adjusted to pH 7 with acetic acid and then concentrated under reduced pressure to remove solvent. The residue is dissolved in a mixture of ethyl acetate and water and the organic layer is collected therefrom. The organic layer is washed with an aqueous saturated sodium chloride solution, dried and concentrated to remove solvent. The residue is distilled under reduced pressure, whereby methyl 2-isocyano-2-(2-thienylmethyl)butyrate (7.7 g) is obtained as pale yellow oil.

Aufarbeitung

  1. stirringThe mixture is stirred at room temperature for 4 hours
  2. concentrationconcentrated under reduced pressure
  3. customto remove solvent
  4. dissolutionThe residue is dissolved in a mixture of ethyl acetate and water
  5. customthe organic layer is collected
  6. washThe organic layer is washed with an aqueous saturated sodium chloride solution
  7. customdried
  8. concentrationconcentrated
  9. customto remove solvent
  10. distillationThe residue is distilled under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-759e756f67714c06833db969e245f1ad
Quelldatensatz
uspto-grants-1989_08
Patentnummer
US04857543

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