Acetophenone → 3-[5-(3-Oxo-3-phenyl-propenyl)-pyridin-2-yl]-acrylic acid tert-butyl ester

HRID 556289Notes

Reaction equation

[C:1]([O:5][C:6](=[O:17])[CH:7]=[CH:8][C:9]1[CH:14]=[CH:13][C:12]([CH:15]=O)=[CH:11][N:10]=1)([CH3:4])([CH3:3])[CH3:2].[C:18]([C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)(=[O:20])[CH3:19].[OH-].[K+]>CO>[C:1]([O:5][C:6](=[O:17])[CH:7]=[CH:8][C:9]1[CH:14]=[CH:13][C:12]([CH:15]=[CH:19][C:18](=[O:20])[C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)=[CH:11][N:10]=1)([CH3:4])([CH3:3])[CH3:2]

Participants

Conditions

Temperature: 0 °C

Procedure

3-(5-formyl-pyridin-2-yl)-acrylic acid tert-butyl ester (364 mg, 1.56 mmol) was dissolved in MeOH (10 ml) and the solution was cooled to 0° C. Acetophenone (188 mg, 1.56 mmol) and 1.7M KOH (1.8 ml) were added. The reaction was stirred at 0° C. for 3 h. The resulting solid was filtered on a Buckner funnel to give 130 mg of 3-[5-(3-oxo-3-phenyl-propenyl)-pyridin-2-yl]-acrylic acid tert-butyl ester as a yellow powder.

Workup

filtrationThe resulting solid was filtered on a Buckner funnel

Sources & evidence

ORD record: ord-fe5c3b8aa720431f8c9998c93397f57f
Source dataset: uspto-grants-2011_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08058273B2

Reaction notes

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