Water ethanol → (2Z,4E)-5-(5-Chlorobenzofuran-2-yl)-2-methoxy-2,4-pentadienoic acid
Reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[O:9][C:8](/[CH:10]=[CH:11]/[CH:12]=[C:13](\[O:18][CH3:19])/[C:14]([O:16]C)=[O:15])=[CH:7][C:6]=2[CH:20]=1.CCO.O>>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[O:9][C:8](/[CH:10]=[CH:11]/[CH:12]=[C:13](\[O:18][CH3:19])/[C:14]([OH:16])=[O:15])=[CH:7][C:6]=2[CH:20]=1Participants
3
Procedure
To a stirred solution of methyl (2Z,4E)-5-(5-chlorobenzofuran-2-yl)-2-methoxy-2,4-pentadienoate (530 mg, 1.81 mmol) in EtOH/water 1/1 (40 ml) potassium hydroxide (0.43 g, 7.66 mmol) was added. The solution was stirred at RT overnight, then it was treated as seen in example 2. Pure title compound (330 mg, 1.18 mmol, yield 65.4%) was obtained as bright yellow crystals.
Workup
- additionit was treated