Acetyl chloride → Ethyl benzo[b]thiophene-7-carboxylate

HRID 2261819Notes

Reaction equation

HRID 2261819 reaction equation
[C:1](Cl)(=[O:3])[CH3:2].[S:5]1[CH:9]=[CH:8][C:7]2[CH:10]=[CH:11][CH:12]=[C:13]([C:14](O)=[O:15])[C:6]1=2>C(O)C>[CH2:1]([O:3][C:14]([C:13]1[C:6]2[S:5][CH:9]=[CH:8][C:7]=2[CH:10]=[CH:11][CH:12]=1)=[O:15])[CH3:2]

Participants

4

Reactant 2

HCID 6367Acetyl chlorideHCID 142350731-Benzothiophene-7-carboxylic acid

Product 1

HCID 49758023Ethyl benzo[b]thiophene-7-carboxylateYield 92%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Acetyl chloride (14.8 mmol; 1.05 mL) is added to a solution of benzo[b]thiophene-7-carboxylic acid (4.94 mmol; 880 mg) in ethanol (20 mL) and the mixture is stirred at reflux for 24 h. The solvent is removed. Ethyl acetate is added to the residue and the resulting solution is washed with water, dried (Na2SO4), filtered and concentrated to obtain the title compound (880 mg, 92%) as colorless oil. 1H NMR (CDCl3): δ 8.12 (dd, 1H, J=7.2 Hz, 0.6 Hz), 8.03 (dd, 1H, J=7.6 Hz, 1.2 Hz), 7.58 (d, 1H, J=5.6 Hz), 7.46 (t, 1H, J=7.6 Hz), 7.41 (t, 1H, J=5.2 Hz), 4.50 (c, 2H, J=7.3 Hz), 1.47 (t, 3H, J=7.3 Hz).

Workup

  1. temperatureat reflux for 24 h
  2. customThe solvent is removed
  3. additionEthyl acetate is added to the residue
  4. washthe resulting solution is washed with water
  5. dry with materialdried (Na2SO4)
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-39d83e3a06574f119f83b3f9a99f51c5
Source dataset
uspto-grants-2010_12
Patent number
US07846960B2

Reaction notes

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