Hydrochloric Acid → Ethyl benzo[b]thiophene-5-carboxylate

HRID 250243Notes

Reaction equation

HRID 250243 reaction equation
Cl.[S:2]1[C:6]2[CH:7]=[CH:8][C:9]([C:11]([OH:13])=[O:12])=[CH:10][C:5]=2[CH:4]=[CH:3]1.[CH2:14](O)[CH3:15]>>[CH2:14]([O:12][C:11]([C:9]1[CH:8]=[CH:7][C:6]2[S:2][CH:3]=[CH:4][C:5]=2[CH:10]=1)=[O:13])[CH3:15]

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 702EthanolHCID 27954441-Benzothiophene-5-carboxylic acid

Product 1

HCID 14792358Ethyl benzo[b]thiophene-5-carboxylateYield 89%

Conditions

Temperature
80 °C

Procedure

A saturated solution of HCl in ethanol (15 mL) is added to benzothiophene-5-carboxylic acid (1 g, 5.44 mmol) and the reaction mixture is stirred at 80° C. overnight. The solvent is removed under reduced pressure and diethyl ether and saturated sodium bicarbonate are added to the residue. The layers are separated. The organic layer is washed with saturated sodium bicarbonate and water, dried over anhydrous sodium sulfate, filtered, and concentrated under reduced pressure to yield the title compound (1.0 g, 89%) as a pale brown oil. 1H NMR (CDCl3): δ 8.54 (s, 1H), 8.01 (d, 1H, J=8.1 Hz), 7.92 (d, 1H, J=8.1 Hz), 7.51 (d, 1H, J=5.4 Hz), 7.42 (d, 1H, J=5.4 Hz), 4.42 (c, 2H, J=6.8 Hz), 1.43 (t, 3H, J=6.8 Hz).

Workup

  1. customThe solvent is removed under reduced pressure and diethyl ether and saturated sodium bicarbonate
  2. additionare added to the residue
  3. customThe layers are separated
  4. washThe organic layer is washed with saturated sodium bicarbonate and water
  5. dry with materialdried over anhydrous sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-a58832ce62644a6bbb2b60a0d4f2fd8f
Source dataset
uspto-grants-2011_01
Patent number
US07863302B2

Reaction notes

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