Sodium Hydroxide → (E)-3-[5,6Dimethoxy-3-(4-methoxyphenoxy)benzo[b]thiophen-2-yl]-2-(4-pyridinyl)-2-propenoic acid

HRID 1004118Notes

Reaction equation

HRID 1004118 reaction equation
[CH3:1][O:2][C:3]1[C:33]([O:34][CH3:35])=[CH:32][C:6]2[S:7][C:8](/[CH:19]=[C:20](\[C:26]3[CH:31]=[CH:30][N:29]=[CH:28][CH:27]=3)/[C:21]([O:23]CC)=[O:22])=[C:9]([O:10][C:11]3[CH:16]=[CH:15][C:14]([O:17][CH3:18])=[CH:13][CH:12]=3)[C:5]=2[CH:4]=1.[OH-].[Na+]>C(O)C>[CH3:1][O:2][C:3]1[C:33]([O:34][CH3:35])=[CH:32][C:6]2[S:7][C:8](/[CH:19]=[C:20](\[C:26]3[CH:27]=[CH:28][N:29]=[CH:30][CH:31]=3)/[C:21]([OH:23])=[O:22])=[C:9]([O:10][C:11]3[CH:12]=[CH:13][C:14]([O:17][CH3:18])=[CH:15][CH:16]=3)[C:5]=2[CH:4]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 86755303Ethyl (E)-3-[5,6-dimethoxy-3-(4-methoxyphenoxy)benzo[b]thiophen-2-yl]-2-(4-pyridinyl)-2-propenoate

Product 1

HCID 9912231(E)-3-[5,6Dimethoxy-3-(4-methoxyphenoxy)benzo[b]thiophen-2-yl]-2-(4-pyridinyl)-2-propenoic acid

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution containing 3 mmol of the product of Example 1, 6 ml of an aqueous 1N sodium hydroxide solution and 20 ml of ethanol is refluxed for 2 hours. After returning to room temperature, the reaction mixture is concentrated under reduced pressure and the residue is then diluted in water and subsequently taken up in diethyl ether. The organic phase is then rendered acidic by the addition of 6 ml of a 1N HCl solution. A precipitate forms, which is filtered, rinsed with water and then dried under reduced pressure, enabling 1.3 g of the expected compound to be obtained.

Workup

  1. temperatureis refluxed for 2 hours
  2. customAfter returning to room temperature
  3. concentrationthe reaction mixture is concentrated under reduced pressure
  4. additionthe residue is then diluted in water
  5. additionrendered acidic by the addition of 6 ml of a 1N HCl solution
  6. filtrationA precipitate forms, which is filtered
  7. washrinsed with water
  8. customdried under reduced pressure
  9. customto be obtained

Sources & evidence

ORD record
ord-3c3fab9e81904ad1b01f910d246bfe71
Source dataset
uspto-grants-2000_04
Patent number
US06048875

Reaction notes

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