Potassium Carbonate → HCID 59559946, compound

HRID 1177310Notes

Reaction equation

HRID 1177310 reaction equation
C([O:4][C:5]1[C:13]2[O:12][C:11]([CH3:14])=[CH:10][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:13]2[O:12][C:11]([CH3:14])=[CH:10][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 59560071HCID 59560071, compound

Product 1

HCID 59559946HCID 59559946, compoundYield 81%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
60 °C

Procedure

Ethyl 7-(Acetyloxy)-2-methyl-1-benzofuran-5-carboxylate was dissolved in absolute ethanol (200 mL). Potassium carbonate (18 g, 0.13 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 residue was and crystallized from ether/hexane mixture, 1:5 to give the desired product 8.5 g (38 mmol, 81%) as a cream solid. 1H NMR (DMSO-D6): δ ppm 1.35 (t, 3H), 2.40 (s, 3H), 4.20 (qt, 2H), 6.65 (s, 1H), 7.32 (s, 1H), 7.65 (s, 1H); MS (APCI, pos): 221.1.

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. customcrystallized from ether/hexane mixture, 1:5

Sources & evidence

ORD record
ord-71bc03de1ef74a879e9b5bc620a447f9
Source dataset
uspto-grants-2010_11
Patent number
US07842713B2

Reaction notes

Loading…