Dimethylformamide → 2-(2-Cyanoethylidene)-bicyclo[2.2.1]heptane

HRID 1448720

Reaktionsgleichung

Reaktionsgleichung von HRID 1448720
[CH:1]([CH:3]1[CH2:8][CH:7]2[CH2:9][CH:4]1[CH2:5][CH2:6]2)=O.[C:10]([CH2:12]C(O)=O)#[N:11].[OH-].[NH4+].CN(C)C=O>C1C=CC=CC=1>[C:10]([CH2:12][CH:1]=[C:3]1[CH2:8][CH:7]2[CH2:9][CH:4]1[CH2:5][CH2:6]2)#[N:11]

Komponenten

6

Edukt 4

HCID 6228DimethylformamideHCID 9740Cyanoacetic acidHCID 14923Ammonium HydroxideHCID 86864Bicyclo[2.2.1]heptane-2-carbaldehyde

Produkt 1

HCID 544239752-(2-Cyanoethylidene)-bicyclo[2.2.1]heptaneAusbeute 79 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 241BenzeneLösungsmittel

Versuchsvorschrift

A stirred solution of 95 g (0.77 mol) of 2-formylbicyclo[2.2.1]heptane, 65 g (0.76 mol) of cyanoacetic acid, 2 ml of ammonium hydroxide (58%), 132 ml of dimethylformamide, and 170 ml benzene was heated to reflux and the water removed with a Dean-Stark trap. The reaction was allowed to continue until the evolution of carbon dioxide ceased (approx. 24 hrs.). Upon completion, the reaction was cooled and the solvent removed under reduced pressure. The residual oil was distilled under vacuum to give 88 g (79% yield) of 2-(2-cyanoethylidene)-bicyclo[2.2.1]heptane: b.p. 72°-80° C./1 mm; ir 2960, 2870, 2260, 1685, 1450, 1420, 1305, 920; nmr 1.15-2.8 (10H, m), 2.96 (2H, m), 4.9-5.4 (1H, m); ms 147.

Aufarbeitung

  1. temperatureto reflux
  2. customthe water removed with a Dean-Stark trap
  3. custom(approx. 24 hrs.)
  4. temperatureUpon completion, the reaction was cooled
  5. customthe solvent removed under reduced pressure
  6. distillationThe residual oil was distilled under vacuum

Quellen und Nachweise

ORD-Eintrag
ord-82330359a3174551a5716949c44cf368
Quelldatensatz
uspto-grants-1980_02
Patentnummer
US04187243

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