Tetrahydrofuran → HCID 89767975, compound

HRID 591539Notes

Reaction equation

HRID 591539 reaction equation
C[O:2][C:3](=[O:24])[CH2:4][C:5]1[C:9]2[CH:10]=[CH:11][C:12]([O:14][CH2:15][C:16]3[C:17]([CH3:23])=[N:18][C:19]([CH3:22])=[CH:20][CH:21]=3)=[CH:13][C:8]=2[O:7][CH:6]=1.[OH-].[Na+].C1COCC1>CO>[CH3:23][C:17]1[C:16]([CH2:15][O:14][C:12]2[CH:11]=[CH:10][C:9]3[C:5]([CH2:4][C:3]([OH:24])=[O:2])=[CH:6][O:7][C:8]=3[CH:13]=2)=[CH:21][CH:20]=[C:19]([CH3:22])[N:18]=1

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 14798Sodium HydroxideHCID 118667055HCID 118667055, compound

Product 1

HCID 89767975HCID 89767975, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of methyl(6-((2,6-dimethylpyridin-3-yl)methoxy)-1-benzofuran-3-yl)acetate (430 mg), 1N NaOH (5 mL), THF (5 mL) and MeOH (5 mL) was stirred at room temperature for 1 h. The mixture was washed with Et2O. Water and 1N HCl (5 mL) were added to the water layer to be pH=4. The precipitate was collected by filtration and washed with water and Et2O respectively to give crystals. The crystals were recrystallized from acetone-hexane to give the title compound.

Workup

  1. washThe mixture was washed with Et2O
  2. additionWater and 1N HCl (5 mL) were added to the water layer
  3. filtrationThe precipitate was collected by filtration
  4. washwashed with water and Et2O respectively
  5. customto give crystals
  6. customThe crystals were recrystallized from acetone-hexane

Sources & evidence

ORD record
ord-9a2e8e820a214f75813eeb6cd3ae1a63
Source dataset
uspto-grants-2016_01
Patent number
US09238639B2

Reaction notes

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