(Nitromethyl)benzene → 6-Nitro-6-phenylhex-5-enal

HRID 1193016

Reaction equation

HRID 1193016 reaction equation
[N+:1]([CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)([O-:3])=[O:2].C[O:12][CH:13](OC)[CH2:14][CH2:15][CH2:16][CH:17]=O>CCOC(C)=O.CCCCCC>[N+:1]([C:4]([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)=[CH:17][CH2:16][CH2:15][CH2:14][CH:13]=[O:12])([O-:3])=[O:2]

Participants

4

Reactant 2

HCID 69321(Nitromethyl)benzeneHCID 170903Pentanal, 5,5-dimethoxy-

Product 1

HCID 765529406-Nitro-6-phenylhex-5-enalYield 41.1%

Reagents, catalysts & solvents 1

HCID 21226206Ethyl acetate hexaneSolvent

Procedure

Prepared according to the general procedure B from 1-(nitromethyl)benzene 112d (24 mmol) and 5,5-dimethoxypentanal 131 (16 mmol) to provide the title compound as yellow oil (E/Z=6.7/1) (1.44 g, 41% yield) after silica gel chromatography (EtOAc/Hexane).

Workup

  1. customPrepared

Sources & evidence

ORD record
ord-088268a327994039bea3fca27f7f92b0
Source dataset
uspto-grants-2014_03
Patent number
US08680335B2

Linked notes

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