Water ethanol → (2Z,4E)-5-(5-Chlorobenzofuran-2-yl)-2-methoxy-2,4-pentadienoic acid

HRID 377371Notes

Reaction equation

HRID 377371 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]=1

Participants

3

Reactant 2

HCID 19096565Water ethanolHCID 86755125HCID 86755125, compound

Product 1

HCID 19358675(2Z,4E)-5-(5-Chlorobenzofuran-2-yl)-2-methoxy-2,4-pentadienoic acidYield 65.4%

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

  1. additionit was treated

Sources & evidence

ORD record
ord-8741bc70ae044fa29754305e64247e5d
Source dataset
uspto-grants-2000_02
Patent number
US06025390

Reaction notes

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