Hydrochloric Acid → Ethyl 2-(6-((2,6-dimethylpyridin-3-yl)methoxy)-1-benzothiophen-3-yl)propanoate

HRID 591505Notes

Reaction equation

HRID 591505 reaction equation
[CH2:1]([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)[CH3:2].IC.[H-].[Na+].Cl.[C:31]([O-])(O)=O.[Na+]>C1COCC1>[CH3:24][C:18]1[C:17]([CH2:16][O:15][C:13]2[CH:12]=[CH:11][C:10]3[C:6]([CH:5]([CH3:31])[C:4]([O:3][CH2:1][CH3:2])=[O:25])=[CH:7][S:8][C:9]=3[CH:14]=2)=[CH:22][CH:21]=[C:20]([CH3:23])[N:19]=1

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 516892Sodium BicarbonateHCID 118667000Ethyl(6-((2,6-dimethylpyridin-3-yl)methoxy)-1-benzothiophen-3-yl)acetate

Product 1

HCID 89767811Ethyl 2-(6-((2,6-dimethylpyridin-3-yl)methoxy)-1-benzothiophen-3-yl)propanoate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a mixture of ethyl(6-((2,6-dimethylpyridin-3-yl)methoxy)-1-benzothiophen-3-yl)acetate (710 mg) and iodomethane (0.373 ml) and THF (10 mL) was added sodium hydride (60% in oil, 160 mg) at 0° C. The mixture was stirred 0° C. to room temperature under argon atmosphere overnight. To the mixture was added 1N HCl at room temperature, and the mixture was adjusted to pH 6-7 with saturated aqueous NaHCO3 and extracted with EtOAc. The organic layer was washed successively with brine and water, dried over Na2SO4 and concentrated in vacuo. The residue was purified by silica gel column chromatography (EtOAc/hexane) to give the title compound (230 mg).

Workup

  1. extractionextracted with EtOAc
  2. washThe organic layer was washed successively with brine and water
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified by silica gel column chromatography (EtOAc/hexane)

Sources & evidence

ORD record
ord-06f7476422c84b6f97284cf287ee1d6a
Source dataset
uspto-grants-2016_01
Patent number
US09238639B2

Reaction notes

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