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

HRID 250244Notes

Reaction equation

HRID 250244 reaction equation
[C:1](Cl)(=O)C.[S:5]1[CH:9]=[CH:8][C:7]2[CH:10]=[CH:11][CH:12]=[C:13]([C:14]([OH:16])=[O:15])[C:6]1=2>CO>[CH3:1][O:15][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:16]

Participants

4

Reactant 2

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

Product 1

HCID 13759324Methyl benzo[b]thiophene-7-carboxylateYield 92.7%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

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 methanol (20 mL). The reaction mixture is stirred at reflux for 24 h. The solvent is removed under reduced pressure. The residue is taken up in ethyl acetate washed with water, dried over anhydrous sodium sulfate, filtered, and concentrated under reduced pressure to yield 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), 4.03 (s, 3H).

Workup

  1. temperatureat reflux for 24 h
  2. customThe solvent is removed under reduced pressure
  3. washwashed with water
  4. dry with materialdried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-adcff69f4bcf41929d8e684b72b7cea0
Source dataset
uspto-grants-2011_01
Patent number
US07863302B2

Reaction notes

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