Potassium Carbonate → HCID 11528799, compound

HRID 1643802Notes

Reaction equation

HRID 1643802 reaction equation
C([O:4][C:5]1[C:10]2[CH:11]=[C:12]([CH3:14])[S:13][C:9]=2[CH:8]=[C:7]([C:15]([O:17][CH2:18][CH3:19])=[O:16])[CH:6]=1)(=O)C.C(=O)([O-])[O-].[K+].[K+]>C(O)C.ClCCl>[CH2:18]([O:17][C:15]([C:7]1[CH:6]=[C:5]([OH:4])[C:10]2[CH:11]=[C:12]([CH3:14])[S:13][C:9]=2[CH:8]=1)=[O:16])[CH3:19]

Participants

5

Reactant 2

HCID 11430Potassium CarbonateHCID 59559982HCID 59559982, compound

Product 1

HCID 11528799HCID 11528799, compoundYield 79%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
60 °C

Procedure

Ethyl 4-(acetyloxy)-2-methyl-1-benzothiophene-6-carboxylate was dissolved in absolute ethanol (200 mL). Potassium carbonate (7 g, 50 mmol) was added. The reaction mixture was stirred for 3 h at 60° C. and diluted with 200 mL of dichloromethane. The suspension was filtered. The precipitate was washed by 100 mL of dichloromethane. The combined solutions were washed by 200 mL of a 10% aqueous solution of citric acid and evaporated in vacuum to dryness. The obtained crude product was chromatographed on a layer of silica gel (150×100 mm) with hexane/ethyl acetate mixture, 2:1 as eluent to give 5.5 g (23 mmol, 79%) of 4-Hydroxy-2-methyl-1-benzothiophene-6-carboxylate ethyl ester as a cream solid.

Workup

  1. filtrationThe suspension was filtered
  2. washThe precipitate was washed by 100 mL of dichloromethane
  3. washThe combined solutions were washed by 200 mL of a 10% aqueous solution of citric acid
  4. customevaporated in vacuum to dryness
  5. customThe obtained crude product
  6. customwas chromatographed on a layer of silica gel (150×100 mm) with hexane/ethyl acetate mixture, 2:1 as eluent

Sources & evidence

ORD record
ord-80e8abb742364e908883667d76c451c1
Source dataset
uspto-grants-2012_02
Patent number
US08119624B2

Reaction notes

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