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

HRID 2261816Notes

Reaction equation

HRID 2261816 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 stirred at 80° C. overnight. The solvent is removed under reduced pressure. Diethyl ether and saturated sodium bicarbonate are added. The aqueous layer is discarded. The organic layer is washed with saturated sodium bicarbonate and water, dried (Na2SO4), filtered, and concentrated under reduced pressure to yield the title compound as a pale brown oil (1.0 g, 89%). 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
  2. additionDiethyl ether and saturated sodium bicarbonate are added
  3. washThe organic layer is washed with saturated sodium bicarbonate and water
  4. dry with materialdried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-c4c793208c8a4934ba5c422f1f138cea
Source dataset
uspto-grants-2010_12
Patent number
US07846960B2

Reaction notes

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