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

HRID 377375Notes

Reaction equation

HRID 377375 reaction equation
[S:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[CH:3]=[C:2]1/[CH:10]=[CH:11]/[CH:12]=[C:13](\[O:18][CH3:19])/[C:14]([O:16]C)=[O:15].CCO.O>>[S:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[CH:3]=[C:2]1/[CH:10]=[CH:11]/[CH:12]=[C:13](\[O:18][CH3:19])/[C:14]([OH:16])=[O:15]

Participants

3

Reactant 2

HCID 19096565Water ethanolHCID 86755127methyl (2Z,4E)-5-(benzothiophen-2-yl)-2-methoxy-2,4-pentadienoate

Product 1

HCID 19358669(2Z,4E)-5-(Benzothiophen-2-yl)-2-methoxy-2,4-pentadienoic acidYield 53.2%

Procedure

To a stirred solution of methyl (2Z,4E)-5-(benzothiophen-2-yl)-2-methoxy-2,4-pentadienoate (107 mg, 0.39 mmol) in EtOH/water 1/1 (10 ml) potassium hydroxide (47 mg, 0.78 mmol) was added. The solution was refluxed for 1 hour, then it was treated as seen in example 2. Pure title compound (54 mg, 0.207 mmol, yield 53.2%) was obtained as yellow crystals.

Workup

  1. temperatureThe solution was refluxed for 1 hour
  2. additionit was treated

Sources & evidence

ORD record
ord-13a3e85f075d40c082d1865f5650bf03
Source dataset
uspto-grants-2000_02
Patent number
US06025390

Reaction notes

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