2-Nitropropane → Ethyl 1-Cyano-2,2-dimethyl-3-isobutylcyclopropanecarboxylate

HRID 1285518Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1285518
[C:1](/[C:3](=[CH:9]\[CH2:10][CH:11]([CH3:13])[CH3:12])/[C:4]([O:6][CH2:7][CH3:8])=[O:5])#[N:2].[N+]([CH:17]([CH3:19])[CH3:18])([O-])=O.[O-]CC.[Na+]>C(O)C>[C:1]([C:3]1([C:4]([O:6][CH2:7][CH3:8])=[O:5])[CH:9]([CH2:10][CH:11]([CH3:12])[CH3:13])[C:17]1([CH3:19])[CH3:18])#[N:2]

Komponenten

5

Edukt 3

HCID 3982-NitropropaneHCID 2723922Sodium ethoxideHCID 11019475(E)-Ethyl 2-Cyano-5-methyl-2-hexenoate

Produkt 1

HCID 13429896Ethyl 1-Cyano-2,2-dimethyl-3-isobutylcyclopropanecarboxylateAusbeute 95,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

A mixture of 490 mg (2.70 mmoles) of cyanoester 5 (produced in accordance with Example V), 0.25 mL (2.78 mmoles) of 2-nitropropane, and 4.0 mL of an 0.65M solution of sodium ethoxide (prepared from sodium metal and ethyl alcohol) in absolute ethyl alcohol was heated at reflux, protected from atmospheric moisture, for 31/2 hours. The product was isolated as described in the procedure of Example VIII, affording 575 mg (95% yield) of cyclopropanoid cyanoester 14: bp 80°-102° C. (bath temperature, 0.05 mm).

Aufarbeitung

  1. temperaturewas heated
  2. temperatureat reflux
  3. custom2 hours
  4. customThe product was isolated

Quellen und Nachweise

ORD-Eintrag
ord-fe7f73134dc14964b0c58cb8fb44097a
Quelldatensatz
uspto-grants-1986_01
Patentnummer
US04567265

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