Ethanol → Ethyl 5-acetylthiophene-2-carboxylate

HRID 572262Notes

Reaction equation

HRID 572262 reaction equation
[C:1]([C:4]1[S:8][C:7]([C:9]([OH:11])=[O:10])=[CH:6][CH:5]=1)(=[O:3])[CH3:2].OS(O)(=O)=O.[CH2:17](O)[CH3:18]>>[CH2:17]([O:10][C:9]([C:7]1[S:8][C:4]([C:1](=[O:3])[CH3:2])=[CH:5][CH:6]=1)=[O:11])[CH3:18]

Participants

4

Reactant 3

HCID 702EthanolHCID 1118Sulfuric AcidHCID 37427275-Acetylthiophene-2-carboxylic acid

Product 1

HCID 18737820Ethyl 5-acetylthiophene-2-carboxylateYield 84%

Procedure

A solution of 5-acetylthiophene-2-carboxylic acid (17.0 g, 100 mmol) in ethanol (500 mL) was treated with a concentrated H2SO4 solution (10 mL) and heated at reflux for 3 days after which time the reaction was evaporated to approximately ¼ volume and partitioned between EtOAc (300 mL) and water (100 mL). The organic portion was then further washed with a saturated aqueous solution of NaHCO3 (2×100 mL) followed by a brine solution (100 mL), then dried over MgSO4, filtered, and evaporated in vacuo to afford product as light brown colored solid (25.0 g, 84%). 1H NMR (CDCl3) 1.39 (t, J=7.0, 3H), 2.59 (s, 3H), 4.38 (q, J=7.3, 2H), 7.64 (d, J=4.0, 1H), 7.76 (d, J=4.0, 1H). 13C NMR 14.3, 27.1, 61.9, 131.8, 133.3, 140.3, 148., 161.7, 190.9. LC/MS 5.47 min, [M+1]+ 199.

Workup

  1. temperatureheated
  2. temperatureat reflux for 3 days after which time the reaction
  3. customwas evaporated to approximately ¼ volume
  4. custompartitioned between EtOAc (300 mL) and water (100 mL)
  5. washThe organic portion was then further washed with a saturated aqueous solution of NaHCO3 (2×100 mL)
  6. dry with materialdried over MgSO4
  7. filtrationfiltered
  8. customevaporated in vacuo

Sources & evidence

ORD record
ord-1a0191211ad24aff8e28af483ac52655
Source dataset
uspto-grants-2015_05
Patent number
US09029397B2

Reaction notes

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