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Diethyl (cyanomethyl)phosphonate → 1-(Cyanomethyl)-3-(cyanomethylene)cyclobutanecarbonitrile

HRID 1966156
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1966156
CC(C)([O-])C.[K+].[C:7]([CH2:9]P(=O)(OCC)OCC)#[N:8].[C:18]([CH2:20][C:21]1([C:26]#[N:27])[CH2:24][C:23](=O)[CH2:22]1)#[N:19]>O1CCCC1>[C:18]([CH2:20][C:21]1([C:26]#[N:27])[CH2:24][C:23](=[CH:9][C:7]#[N:8])[CH2:22]1)#[N:19]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

5

Edukt 3

HCID 75676Diethyl (cyanomethyl)phosphonateHCID 23665647Potassium tert-butoxideHCID 668242591-(Cyanomethyl)-3-oxocyclobutanecarbonitrile

Produkt 1

HCID 866635061-(Cyanomethyl)-3-(cyanomethylene)cyclobutanecarbonitrile

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel3×

Versuchsvorschrift

To a solution of 1.0 M of potassium tert-butoxide in tetrahydrofuran (2.15 mL) at 0° C. was added dropwise a solution of diethyl cyanomethylphosphonate (0.364 mL, 0.00225 mol) in tetrahydrofuran (4 mL, 0.04 mol). The reaction was warmed to rt and then cooled to 0° C. again. To the reaction mixture was added a solution of 1-(cyanomethyl)-3-oxocyclobutanecarbonitrile (0.274 g, 0.00204 mol) in tetrahydrofuran (2 mL, 0.02 mol). The reaction was allowed to warm up to rt and stirred at rt overnight. After quenching with water, the mixture was extracted with ether. The combined organic layers were washed with water and brine, then dried and evaporated to dryness. The crude mixture was used directly in next step.

Aufarbeitung

  1. temperaturecooled to 0° C. again
  2. temperatureto warm up to rt
  3. customAfter quenching with water
  4. extractionthe mixture was extracted with ether
  5. washThe combined organic layers were washed with water and brine
  6. customdried
  7. customevaporated to dryness

Quellen und Nachweise

ORD-Eintrag
ord-1ecc81b8e0754cb59ca81bb28a66fadd
Quelldatensatz
uspto-grants-2013_04
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08420629B2

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