Nitromethane → (E)-6-nitrohex-5-enal

HRID 1193013Notes

Reaction equation

HRID 1193013 reaction equation
[N+:1]([CH3:4])([O-:3])=[O:2].C[O:6][CH:7](OC)[CH2:8][CH2:9][CH2:10][CH:11]=O>CCOC(C)=O.CCCCCC>[N+:1](/[CH:4]=[CH:11]/[CH2:10][CH2:9][CH2:8][CH:7]=[O:6])([O-:3])=[O:2]

Participants

4

Reactant 2

HCID 6375NitromethaneHCID 170903Pentanal, 5,5-dimethoxy-

Product 1

HCID 57516560(E)-6-nitrohex-5-enalYield 66%

Reagents, catalysts & solvents 1

HCID 21226206Ethyl acetate hexaneSolvent

Procedure

Prepared according to the general procedure A from nitromethane 112a (80 mmol) and 5,5-dimethoxypentanal 131 (16 mmol) to provide the title compound as yellow oil (1.51 g, 66% yield) after silica gel chromatography (EtOAc/Hexane).

Workup

  1. customPrepared

Sources & evidence

ORD record
ord-4a9714f50b60466a8e0da7bc31c3558b
Source dataset
uspto-grants-2014_03
Patent number
US08680335B2

Reaction notes

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