Potassium Carbonate → Ethyl 7-Hydroxy-1-benzofuran-5-carboxylate

HRID 1177307Notes

Reaction equation

HRID 1177307 reaction equation
C([O:4][C:5]1[C:13]2[O:12][CH:11]=[CH:10][C:9]=2[CH:8]=[C:7]([C:14]([O:16][CH2:17][CH3:18])=[O:15])[CH:6]=1)(=O)C.C(=O)([O-])[O-].[K+].[K+]>C(O)C.ClCCl>[OH:4][C:5]1[C:13]2[O:12][CH:11]=[CH:10][C:9]=2[CH:8]=[C:7]([C:14]([O:16][CH2:17][CH3:18])=[O:15])[CH:6]=1

Participants

5

Reactant 2

HCID 11430Potassium CarbonateHCID 59560060HCID 59560060, compound

Product 1

HCID 11321696Ethyl 7-Hydroxy-1-benzofuran-5-carboxylateYield 38%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
60 °C

Procedure

Ethyl 7-(Acetyloxy)-1-benzofuran-5-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) to give the desired product 2.8 g (13 mmol, 38%) as a cream solid. 1H NMR (DMSO-D6): δ ppm 1.35 (s, 3H), 4.20 (qt, 2H), 7.15 (m 1H), 7.39 (m, 1H), 7.77 (m, 1H), i8.04 (m, 1H); MS (APCI, pos): 241.1.

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)

Sources & evidence

ORD record
ord-6f6fccef83744d06a8e4333e8d43e91e
Source dataset
uspto-grants-2010_11
Patent number
US07842713B2

Reaction notes

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