Reaction #40813

ord-b4766f87ad664e35965873e1b072eb02

Reaction equation

CC[O-].[Na+]
NaOEt
Cc1ccc(/C=C/C=O)cc1
(E)-3-(4-methylphenyl)acrylaldehyde
Cc1ccc(/C=C/C=O)cc1
Compound 43
Cc1ccc(/C=C/C=O)cc1
(E)-3-(4-methylphenyl)acrylaldehyde
CCOC(=O)CN=[N+]=[N-]
ethyl azidoacetate
→
CCOC(=O)/C(=C/C=C/c1ccc(C)cc1)N=[N+]=[N-]
title compound
CCOC(=O)/C(=C/C=C/c1ccc(C)cc1)N=[N+]=[N-]
Ethyl (2Z,4E)-2-azido-5-(4-methylphenyl)penta-2,4-dienoate

Reactants

—
solution
CC[O-].[Na+]
NaOEt
Cc1ccc(/C=C/C=O)cc1
(E)-3-(4-methylphenyl)acrylaldehyde
Cc1ccc(/C=C/C=O)cc1
Compound 43
Cc1ccc(/C=C/C=O)cc1
(E)-3-(4-methylphenyl)acrylaldehyde
CCOC(=O)CN=[N+]=[N-]
ethyl azidoacetate

Reagents

None

Solvents

CCO
ethanol
CCO
EtOH

Conditions

Detailed conditions
See reaction.notes.procedure_details.

Procedure

Following General Procedure I, a 1.38 M solution of NaOEt in ethanol (30 ml), (E)-3-(4-methylphenyl)acrylaldehyde (Compound 43, 1.1 g, 7.5 mmol) and ethyl azidoacetate (12 ml, 37.5 mmol) in EtOH (20 ml) were reacted to produce the title compound as a solid.

Source

DOI: 10.6084/m9.figshare.5104873.v1Patent: US07728014B2uspto-grants-2010_06