Acetic Acid → Ethyl 3-anilinobut-2-enoate

HRID 222788

Reaction equation

[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:8]([O:14][CH2:15][CH3:16])(=[O:13])[CH2:9][C:10]([CH3:12])=O.C(O)(=O)C>>[NH:1]([C:10]([CH3:12])=[CH:9][C:8]([O:14][CH2:15][CH3:16])=[O:13])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

Reactant 3

HCID 176Acetic Acid

HCID 6115Aniline

HCID 8868Ethyl Acetoacetate

Product 1

HCID 94928Ethyl 3-anilinobut-2-enoate

Procedure

The title compound is commercially available. A mixture of aniline (9.785 mL, 107.4 mmol), ethyl acetoacetate (13.69 mL, 107.4 mmol), and acetic acid (0.6 mL, 10 mmol) was stirred at ambient temperature overnight. It was partitioned between heptane (50 mL) and sat. aq. NaHCO3 solution (50 mL). The organic layer was dried and evaporated to give the title compound of >90% purity that was used in the next steps without further purification.

Workup

customIt was partitioned between heptane (50 mL) and sat. aq. NaHCO3 solution (50 mL)
customThe organic layer was dried
customevaporated

Sources & evidence

ORD record: ord-1e6b975239ce4332973365ad3d45bb4c
Source dataset: uspto-grants-2012_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08207347B2

Linked notes

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