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

HRID 1285518Notes

Reaction equation

HRID 1285518 reaction equation
[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]

Participants

5

Reactant 3

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

Product 1

HCID 13429896Ethyl 1-Cyano-2,2-dimethyl-3-isobutylcyclopropanecarboxylateYield 95.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

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).

Workup

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

Sources & evidence

ORD record
ord-fe7f73134dc14964b0c58cb8fb44097a
Source dataset
uspto-grants-1986_01
Patent number
US04567265

Reaction notes

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