4-Nitrobenzaldehyde → Ethyl 3-(4-nitrophenyl)-2-propenoate

HRID 1582602Notes

Reaction equation

HRID 1582602 reaction equation
[N+:1]([C:4]1[CH:11]=[CH:10][C:7]([CH:8]=O)=[CH:6][CH:5]=1)([O-:3])=[O:2].[C:12]([CH:17]=C1CCP(C2C=CC=CC=2)C1(C1C=CC=CC=1)C1C=CC=CC=1)([O:14][CH2:15][CH3:16])=[O:13]>C(Cl)Cl>[N+:1]([C:4]1[CH:11]=[CH:10][C:7]([CH:8]=[CH:17][C:12]([O:14][CH2:15][CH3:16])=[O:13])=[CH:6][CH:5]=1)([O-:3])=[O:2]

Participants

4

Reactant 2

HCID 5414-NitrobenzaldehydeHCID 68574662(Carbethoxymethylene)triphenylphospholane

Product 1

HCID 95370Ethyl 3-(4-nitrophenyl)-2-propenoateYield 89.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

4-Nitrobenzaldehyde (1 g) was dissolved in methylene chloride (20 ml), and the reaction system was cooled to 0° C. The solution was added with carboethoxymethylenetriphenylphospholan (2.56 g) and stirred at 0° C. for 1 hour. The reaction system was concentrated-under reduced pressure without any treatment, and the residue was purified by silica gel column chromatography (50 g, hexane:ethyl acetate 4:1) to obtain ethyl 3-(4-nitrophenyl)acrylate(1.27 g, 86%).

Workup

  1. customthe residue was purified by silica gel column chromatography (50 g, hexane:ethyl acetate 4:1)

Sources & evidence

ORD record
ord-540fcd9ed78c47a09518722360c52dd7
Source dataset
uspto-grants-2004_05
Patent number
US06737416B2

Reaction notes

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