Hydrochloric Acid → (6-((2,6-Dimethylpyridin-3-yl)methoxy)-1-benzothiophen-3-yl)acetic acid

HRID 591393Notes

Reaction equation

HRID 591393 reaction equation
C([O:3][C:4](=[O:25])[CH2:5][C:6]1[C:10]2[CH:11]=[CH:12][C:13]([O:15][CH2:16][C:17]3[C:18]([CH3:24])=[N:19][C:20]([CH3:23])=[CH:21][CH:22]=3)=[CH:14][C:9]=2[S:8][CH:7]=1)C.[OH-].[Na+].Cl>O.CO.CCO.C1COCC1>[CH3:24][C:18]1[C:17]([CH2:16][O:15][C:13]2[CH:12]=[CH:11][C:10]3[C:6]([CH2:5][C:4]([OH:25])=[O:3])=[CH:7][S:8][C:9]=3[CH:14]=2)=[CH:22][CH:21]=[C:20]([CH3:23])[N:19]=1

Participants

8

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 118667000Ethyl(6-((2,6-dimethylpyridin-3-yl)methoxy)-1-benzothiophen-3-yl)acetate

Product 1

HCID 89767911(6-((2,6-Dimethylpyridin-3-yl)methoxy)-1-benzothiophen-3-yl)acetic acidYield 68.1%

Reagents, catalysts & solvents 4

HCID 702EthanolSolvent2×HCID 887MethanolSolventHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a mixture of ethyl(6-((2,6-dimethylpyridin-3-yl)methoxy)-1-benzothiophen-3-yl)acetate (7.73 g), EtOH (75 mL) and THF (dry) (75 mL) was added 1N NaOH (45 mL). The mixture was stirred at room temperature for 2 h. To the mixture were added EtOH (50 mL) and MeOH (75 mL). The mixture was neutralized with 1N HCl (45 mL), and then water (500 mL) was added dropwise to the mixture. The precipitate was collected by filtration and washed with water. The solid was recrystallized from acetone-hexane to give the title compound (4.85 g).

Workup

  1. filtrationThe precipitate was collected by filtration
  2. washwashed with water
  3. customThe solid was recrystallized from acetone-hexane

Sources & evidence

ORD record
ord-10a9342c5cef44f6b380340875b92242
Source dataset
uspto-grants-2016_01
Patent number
US09238639B2

Reaction notes

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