Methanol → (6-((2,4-Dichlorobenzyl)oxy)-1-benzothiophen-3-yl)acetic acid

HRID 591391Notes

Reaction equation

HRID 591391 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[CH:22]=[CH:21][C:20]([Cl:23])=[CH:19][C:18]=3[Cl:24])=[CH:14][C:9]=2[S:8][CH:7]=1)C.CO.C1COCC1.O.[OH-].[Li+]>O>[Cl:24][C:18]1[CH:19]=[C:20]([Cl:23])[CH:21]=[CH:22][C:17]=1[CH2:16][O:15][C:13]1[CH:12]=[CH:11][C:10]2[C:6]([CH2:5][C:4]([OH:25])=[O:3])=[CH:7][S:8][C:9]=2[CH:14]=1

Participants

6

Reactant 4

HCID 887MethanolHCID 8028TetrahydrofuranHCID 168937Lithium hydroxide, monohydrateHCID 118666999Ethyl(6-((2,4-dichlorobenzyl)oxy)-1-benzothiophen-3-yl)acetate

Product 1

HCID 89767783(6-((2,4-Dichlorobenzyl)oxy)-1-benzothiophen-3-yl)acetic acidYield 95.6%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a mixture of ethyl(6-((2,4-dichlorobenzyl)oxy)-1-benzothiophen-3-yl)acetate (200 mg), MeOH (2.0 mL), THF (dry) (3.0 mL) and water (1.0 mL) was added lithium hydroxide hydrate (63.7 mg). The mixture was stirred at room temperature for 1 h. After the mixture was concentrated, the residue was neutralized with 1M HCl, and the mixture was extracted with EtOAc. The organic layer was washed with brine, dried over MgSO4, filtered, and concentrated in vacuo. The residual solid was crystallized from EtOAc-hexane to give the title compound (177.7 mg).

Workup

  1. concentrationAfter the mixture was concentrated
  2. extractionthe mixture was extracted with EtOAc
  3. washThe organic layer was washed with brine
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe residual solid was crystallized from EtOAc-hexane

Sources & evidence

ORD record
ord-a5fcb297cf184c748eca7cf194d882d6
Source dataset
uspto-grants-2016_01
Patent number
US09238639B2

Reaction notes

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