Sodium Hydroxide → 3-Cyclopropyl-benzo[b]thiophene-2-carboxylic acid

HRID 57163Notes

Reaction equation

HRID 57163 reaction equation
C([O:3][C:4]([C:6]1[S:10][C:9]2[CH:11]=[CH:12][CH:13]=[CH:14][C:8]=2[C:7]=1[CH:15]1[CH2:17][CH2:16]1)=[O:5])C.[OH-].[Na+]>C(O)C>[CH:15]1([C:7]2[C:8]3[CH:14]=[CH:13][CH:12]=[CH:11][C:9]=3[S:10][C:6]=2[C:4]([OH:5])=[O:3])[CH2:16][CH2:17]1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 59651664HCID 59651664, compound

Product 1

HCID 579205163-Cyclopropyl-benzo[b]thiophene-2-carboxylic acidYield 79.9%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of compound 674-B (2.68 g, 10.9 mmol) in ethanol (30 mL) was treated with 3N aqueous sodium hydroxide (5.4 mL, 16.2 mmol) and refluxed for 2 h. The solution was cooled, and the solvent was evaporated in vacuo. The residue was dissolved in water and washed with dichloromethane. The aqueous phase was acidified with concentrated hydrochloric acid, and the product was extracted into ethyl acetate, washed with brine, dried over Na2SO4, filtered and the solvent was evaporated in vacuo, to afford 1.9 g of compound 674-C as a colorless solid. 1H-NMR (DMSO-d6): δ 0.58-1.37 (m, 4H), 2.44-2.47 (m, 1H), 7.13-7.61 (m, 2H), 7.98 (dd, 2H), 13.33 (br s, 1H).

Workup

  1. temperaturerefluxed for 2 h
  2. temperatureThe solution was cooled
  3. customthe solvent was evaporated in vacuo
  4. dissolutionThe residue was dissolved in water
  5. washwashed with dichloromethane
  6. extractionthe product was extracted into ethyl acetate
  7. washwashed with brine
  8. dry with materialdried over Na2SO4
  9. filtrationfiltered
  10. customthe solvent was evaporated in vacuo

Sources & evidence

ORD record
ord-7456505ad86047e18f51e8dc985b56d3
Source dataset
uspto-grants-2016_09
Patent number
US09434711B2

Reaction notes

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