Sodium Hydroxide → 5-Cyano-1-benzothiophene-7-carboxylic acid

HRID 749431Notes

Reaction equation

HRID 749431 reaction equation
[C:1]([C:3]1[CH:4]=[C:5]([C:12]([O:14]CC)=[O:13])[C:6]2[S:10][CH:9]=[CH:8][C:7]=2[CH:11]=1)#[N:2].[OH-].[Na+]>C1COCC1>[C:1]([C:3]1[CH:4]=[C:5]([C:12]([OH:14])=[O:13])[C:6]2[S:10][CH:9]=[CH:8][C:7]=2[CH:11]=1)#[N:2]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 68979189Ethyl 5-cyano-1-benzothiophene-7-carboxylate

Product 1

HCID 586835225-Cyano-1-benzothiophene-7-carboxylic acidYield 87.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Ethyl 5-cyano-1-benzothiophene-7-carboxylate (5.6 g, 24.3 mmol) was dissolved THF (96 mL) and to the resultant solution was added an aqueous solution of NaOH (1.07 g of NaOH in 14 mL of water, 26.7 mmol) at 0° C. The mixture was stirred at room temperature overnight and then most of the solvent was removed by evaporation. The residue was dissolved in an aqueous solution of NaOH (0.1 M). The solution was washed thrice with chloroform, acidified with 2M HCl and then extracted with ethyl acetate. The organic solution was separated and the solvent was evaporated. The residue was flash chromatographed on silica gel (CH2Cl2-MeOH—NH4OH, 8:2:0.5). There was obtained 4.3 g (85%) of 5-cyano-1-benzothiophene-7-carboxylic acid as a tan solid. 1H NMR (500 MHz, DMSO-d6): 7.7 (d, 1H), 8.1 (d, 2H), 8.3 (d, 1H), 8.7 (s, 1H), 14 (b, 1H); LCMS: m/z 202 (M−1)−.

Workup

  1. custommost of the solvent was removed by evaporation
  2. dissolutionThe residue was dissolved in an aqueous solution of NaOH (0.1 M)
  3. washThe solution was washed thrice with chloroform
  4. extractionextracted with ethyl acetate
  5. customThe organic solution was separated
  6. customthe solvent was evaporated
  7. customchromatographed on silica gel (CH2Cl2-MeOH—NH4OH, 8:2:0.5)

Sources & evidence

ORD record
ord-a950e7cc4e5c48dd80367ff413ef359b
Source dataset
uspto-grants-2008_07
Patent number
US07402581B2

Reaction notes

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