Nitroethane → (E)-6-nitrohept-5-enal

HRID 1193014Notes

Reaction equation

HRID 1193014 reaction equation
[N+:1]([CH2:4][CH3:5])([O-:3])=[O:2].CO[CH:8]([O:14]C)[CH2:9][CH2:10][CH2:11][CH:12]=O>CCOC(C)=O.CCCCCC>[N+:1](/[C:4](/[CH3:5])=[CH:12]/[CH2:11][CH2:10][CH2:9][CH:8]=[O:14])([O-:3])=[O:2]

Participants

4

Reactant 2

HCID 6587NitroethaneHCID 170903Pentanal, 5,5-dimethoxy-

Product 1

HCID 58434581(E)-6-nitrohept-5-enalYield 63%

Reagents, catalysts & solvents 1

HCID 21226206Ethyl acetate hexaneSolvent

Procedure

Prepared according to the general procedure A from nitroethane 112b (80 mmol) and 5,5-dimethoxypentanal 131 (16 mmol) to provide the title compound as yellow oil (1.58 g, 63% yield) after silica gel chromatography (EtOAc/Hexane).

Workup

  1. customPrepared

Sources & evidence

ORD record
ord-d71c91091e6146558b44741feab21c83
Source dataset
uspto-grants-2014_03
Patent number
US08680335B2

Reaction notes

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