2-Nitropropane → HCID 13483103, compound

HRID 1285516Notes

Reaction equation

HRID 1285516 reaction equation
[C:1](/[C:3](=[CH:8]\[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)/[C:4]([O:6][CH3:7])=[O:5])#[N:2].[N+]([CH:18]([CH3:20])[CH3:19])([O-])=O.C[O-].[Na+]>CO>[C:1]([C:3]1([C:4]([O:6][CH3:7])=[O:5])[CH:8]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[C:18]1([CH3:20])[CH3:19])#[N:2]

Participants

5

Reactant 3

HCID 3982-NitropropaneHCID 674252Methyl (E)-2-Cyano-3-phenylacrylateHCID 10942334Sodium Methoxide

Product 1

HCID 13483103HCID 13483103, compoundYield 77.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of 511 mg (2.73 mmoles) of cyanoester 2 (produced in accordance with Example II), 0.25 mL (2.78 mmoles) of 2-nitropropane, and 2.64 mmoles of sodium methoxide (prepared from 61 mg of sodium and methyl alcohol) in 4.0 mL of absolute methanol was stirred at room temperature for 10 minutes and subsequently heated at reflux, protected from atmospheric moisture, for 71/2 hours. The product was isolated as described in the procedure of Example VIII, affording 483 mg (77% yield) of cyclopropanoid cyanoester 11, stereochemically homogeneous as shown by NMR analysis: δ3.83 (singlet, CO2CH3) and δ3.30 (singlet, cyclopropyl H).

Workup

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

Sources & evidence

ORD record
ord-7c3487ab0e6740bbbc49ddb176b62665
Source dataset
uspto-grants-1986_01
Patent number
US04567265

Reaction notes

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