Hydrochloric Acid → (6-((2,6-Dimethylpyridin-3-yl)methoxy)-4,7-dimethyl-1-benzofuran-3-yl)acetic acid

HRID 591470Notes

Reaction equation

HRID 591470 reaction equation
C[O:2][C:3](=[O:26])[CH2:4][C:5]1[C:9]2[C:10]([CH3:25])=[CH:11][C:12]([O:15][CH2:16][C:17]3[C:18]([CH3:24])=[N:19][C:20]([CH3:23])=[CH:21][CH:22]=3)=[C:13]([CH3:14])[C:8]=2[O:7][CH:6]=1.CO.[OH-].[Na+].Cl>C1COCC1>[CH3:24][C:18]1[C:17]([CH2:16][O:15][C:12]2[CH:11]=[C:10]([CH3:25])[C:9]3[C:5]([CH2:4][C:3]([OH:26])=[O:2])=[CH:6][O:7][C:8]=3[C:13]=2[CH3:14])=[CH:22][CH:21]=[C:20]([CH3:23])[N:19]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 887MethanolHCID 14798Sodium HydroxideHCID 118667012Methyl(6-((2,6-dimethylpyridin-3-yl)methoxy)-4,7-dimethyl-1-benzofuran-3-yl)acetate

Product 1

HCID 89768019(6-((2,6-Dimethylpyridin-3-yl)methoxy)-4,7-dimethyl-1-benzofuran-3-yl)acetic acidYield 73.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a mixture of methyl(6-((2,6-dimethylpyridin-3-yl)methoxy)-4,7-dimethyl-1-benzofuran-3-yl)acetate (142.0 mg), MeOH (2.0 mL) and THF (dry) (2.0 mL) was added 1N NaOH (1.21 mL) at room temperature. The mixture was stirred at room temperature for 2 h. The mixture was neutralized with 1N HCl. The precipitate was collected by filtration. The solid was crystallized from IPA-EtOAc to give the title compound (100 mg).

Workup

  1. filtrationThe precipitate was collected by filtration
  2. customThe solid was crystallized from IPA-EtOAc

Sources & evidence

ORD record
ord-30e360c292294bfaa1ce6ac85227c166
Source dataset
uspto-grants-2016_01
Patent number
US09238639B2

Reaction notes

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