StartseiteMCPWorkbenchSkills
StartseiteWorkbenchBenachrichtigungenMein Bereich
llms.txt · MCP-AnleitungDatenschutz · Nutzungsbedingungen · Supportv1.8.0
  1. Startseite
  2. /Reaktion

Acetone → Methyl 1-cyanocyclobutane-1-carboxylate

HRID 1805409
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1805409
[C:1]([CH2:3][C:4]([O:6][CH3:7])=[O:5])#[N:2].N12CCCN=C1CC[CH2:11][CH2:10][CH2:9]2.CC(C)=O.BrCCCBr>CN(C=O)C>[CH3:7][O:6][C:4]([C:3]1([C:1]#[N:2])[CH2:11][CH2:10][CH2:9]1)=[O:5]
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 4

HCID 180AcetoneHCID 7747Methyl cyanoacetateHCID 80011,3-DibromopropaneHCID 811841,8-Diazabicyclo(5.4.0)undec-7-ene

Produkt 1

HCID 25918826Methyl 1-cyanocyclobutane-1-carboxylateAusbeute 63 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228
Dimethylformamide
Lösungsmittel
2×

Reaktionsbedingungen

Temperatur
50 °C

Versuchsvorschrift

10 g (0.1 mol) of methyl cyanoacetate and 10 mL of anhydrous DMF were mixed under stirring for 10 minutes, followed by adding 33.4 g (0.22 mol) of 1,8-diazabicyclo[5,4,0] undec-7-ene (DBU) at 10-20° C. into the mixture, heating the mixture to 50° C. to allow reaction to take place for 15 minutes, moving the mixture to an ice bath (−5˜−10° C.) of a mixture of liquid nitrogen and acetone, and adding 20.4 g (0.10 mol) of 1,3-dibromopropane dissolved in 10 mL of anhydrous DMF into the mixture to form a reaction solution. The reaction solution was subjected to reaction at 25° C. for 15 minutes, and to further reaction at 70° C. for 30 minutes, followed by evaporating, extracting with CH2Cl2 and deionized water, collecting an organic layer from the extraction, evaporating, purifying using silica column chromatography (eluent: acetone/hexane=8/1), and re-evaporating to obtain a product of 8.74 g (0.063 mol, 62.85%) of 4.

Aufarbeitung

  1. customreaction
  2. customfor 15 minutes
  3. customto form a reaction solution
  4. customThe reaction solution was subjected to reaction at 25° C. for 15 minutes
  5. customto further reaction at 70° C. for 30 minutes
  6. customby evaporating
  7. extractionextracting with CH2Cl2
  8. customcollecting an organic layer
  9. extractionfrom the extraction
  10. customevaporating
  11. custompurifying
  12. customre-evaporating

Quellen und Nachweise

ORD-Eintrag
ord-55ba8d2473a04ee896027b27cdf05387
Quelldatensatz
uspto-grants-2013_01
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08354512B2

Notizen zur Reaktion

Wird geladen…

Auf dieser SeiteKomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion