Acetic acid, azido-, ethyl ester → Methyl (2Z,4E)-2-Azido-5-(4-isopropylphenyl)penta-2,4-dienoate

HRID 12574

Reaction equation

HRID 12574 reaction equation
C[O-].[Na+].[CH:4]([C:7]1[CH:12]=[CH:11][C:10](/[CH:13]=[CH:14]/[CH:15]=O)=[CH:9][CH:8]=1)([CH3:6])[CH3:5].[N:17]([CH2:20][C:21]([O:23][CH2:24]C)=[O:22])=[N+:18]=[N-:19]>CO>[N:17](/[C:20](=[CH:15]\[CH:14]=[CH:13]\[C:10]1[CH:9]=[CH:8][C:7]([CH:4]([CH3:5])[CH3:6])=[CH:12][CH:11]=1)/[C:21]([O:23][CH3:24])=[O:22])=[N+:18]=[N-:19]

Participants

5

Reactant 3

HCID 69480Acetic acid, azido-, ethyl esterHCID 53548974-Isopropylcinnamaldehyde2×HCID 10942334Sodium Methoxide

Product 1

HCID 59338838Methyl (2Z,4E)-2-Azido-5-(4-isopropylphenyl)penta-2,4-dienoate

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

Following General Procedure I, a 1.34 M solution of NaOMe in methanol (30 ml), (E)-3-(4-isopropylphenyl)acrylaldehyde (Compound 110, 1.4 g, 8.0 mmol) and ethyl azidoacetate (12 ml, 40.2 mmol) in MeOH (20 ml) were reacted to produce the title compound as a solid.

Sources & evidence

ORD record
ord-592b442687364ab1abccb3c7162513dc
Source dataset
uspto-grants-2010_06
Patent number
US07728014B2

Linked notes

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