Hydrochloric Acid → HCID 89767889, compound

HRID 591484Notes

Reaction equation

HRID 591484 reaction equation
C([O:5][C:6](=[O:33])[CH2:7][O:8][C:9]1[C:13]2[CH:14]=[CH:15][C:16]([O:18][CH2:19][C:20]3[CH:25]=[CH:24][C:23]([Cl:26])=[CH:22][C:21]=3[Cl:27])=[CH:17][C:12]=2[S:11][C:10]=1[C:28]([O:30]CC)=[O:29])(C)(C)C.[OH-].[Na+].CCO.Cl>O.C1COCC1>[C:6]([CH2:7][O:8][C:9]1[C:13]2[CH:14]=[CH:15][C:16]([O:18][CH2:19][C:20]3[CH:25]=[CH:24][C:23]([Cl:26])=[CH:22][C:21]=3[Cl:27])=[CH:17][C:12]=2[S:11][C:10]=1[C:28]([OH:30])=[O:29])([OH:33])=[O:5]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 702EthanolHCID 14798Sodium HydroxideHCID 89767477HCID 89767477, compound

Product 1

HCID 89767889HCID 89767889, compoundYield 92.5%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
50 °C

Procedure

A mixture of ethyl 3-(2-tert-butoxy-2-oxoethoxy)-6-((2,4-dichlorobenzyl)oxy)-1-benzothiophene-2-carboxylate (1.1 g), 1N NaOH (5 mL), EtOH (5 mL) and THF (10 mL) was stirred at 50° C. for 24 h. Water and 1N HCl (5 mL) were added to the mixture and the mixture was extracted with THF-EtOAc. The organic layer was washed with brine, dried over MgSO4 and concentrated in vacuo. The residue was washed with hexane to give the title compound (0.850 g). The obtained crystals were recrystallized from acetone-water.

Workup

  1. extractionthe mixture was extracted with THF-EtOAc
  2. washThe organic layer was washed with brine
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated in vacuo
  5. washThe residue was washed with hexane

Sources & evidence

ORD record
ord-71dcd808ac204434a86f1bb59418d602
Source dataset
uspto-grants-2016_01
Patent number
US09238639B2

Reaction notes

Loading…