Potassium Carbonate → HCID 59559893, compound

HRID 1177321Notes

Reaction equation

HRID 1177321 reaction equation
C([O:4][C:5]1[C:10]2[C:11]([CH3:14])=[CH:12][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>[OH:4][C:5]1[C:10]2[C:11]([CH3:14])=[CH:12][S:13][C:9]=2[CH:8]=[C:7]([C:15]([O:17][CH2:18][CH3:19])=[O:16])[CH:6]=1

Participants

5

Reactant 2

HCID 11430Potassium CarbonateHCID 59559896HCID 59559896, compound

Product 1

HCID 59559893HCID 59559893, compoundYield 60%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
60 °C

Procedure

Ethyl 4-(acetyloxy)-3-methyl-1-benzothiophene-6-carboxylate was dissolved in absolute ethanol (500 mL). Potassium carbonate (35 g, 0.25 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) to give the desired product 19.5 g (82 mmol, 60%) as a cream solid. 1H NMR (DMSO-D6): δ ppm 1.35 (t, 3H), 2.60 (s, 3H), 4.20 (qt, 2H), 7.29 (m, 1H), 7.35 (s, 1H), 7.95 (s, 1H); MS (APCI, pos): 237.1.

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-aedde4a6b7c04b338365c2b0f9296284
Source dataset
uspto-grants-2010_11
Patent number
US07842713B2

Reaction notes

Loading…