Ethanol → ethyl 4-hydroxy-1-benzothiophene-6-carboxylate

HRID 1643795Notes

Reaction equation

HRID 1643795 reaction equation
C([O:4][C:5]1[C:10]2[CH:11]=[CH:12][S:13][C:9]=2[CH:8]=[C:7]([C:14]([O-:16])=[O:15])[CH:6]=1)(=O)C.C(=O)([O-])[O-].[K+].[K+].[CH2:23](O)[CH3:24]>ClCCl>[OH:4][C:5]1[C:10]2[CH:11]=[CH:12][S:13][C:9]=2[CH:8]=[C:7]([C:14]([O:16][CH2:23][CH3:24])=[O:15])[CH:6]=1

Participants

5

Reactant 3

HCID 702EthanolHCID 11430Potassium CarbonateHCID 86624768HCID 86624768, compound

Product 1

HCID 11379055ethyl 4-hydroxy-1-benzothiophene-6-carboxylateYield 37%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
60 °C

Procedure

4-(Acetyloxy)-1-benzothiophene-6-carboxylate was dissolved in absolute ethanol (200 mL). Potassium carbonate (14 g, 0.1 mol) 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 6.5 g (29 mmol, 37%) of ethyl 4-hydroxy-1-benzothiophene-6-carboxylate as a cream-colored 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-ed8080ba02924d84a09440329127b8fd
Source dataset
uspto-grants-2012_02
Patent number
US08119624B2

Reaction notes

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