Potassium Carbonate → HCID 22990152, compound

HRID 1169457Notes

Reaction equation

HRID 1169457 reaction equation
[CH2:1]([O:3][CH2:4][CH2:5][O:6][C:7]1[CH:31]=[CH:30][C:10]([CH2:11][O:12][C:13]2[CH:14]=[CH:15][C:16]3[S:22](=[O:24])(=[O:23])[CH2:21][CH2:20][C:19]([C:25]([O:27]C)=[O:26])=[CH:18][C:17]=3[CH:29]=2)=[CH:9][CH:8]=1)[CH3:2].C(=O)([O-])[O-].[K+].[K+]>C1COCC1.CO>[CH2:1]([O:3][CH2:4][CH2:5][O:6][C:7]1[CH:8]=[CH:9][C:10]([CH2:11][O:12][C:13]2[CH:14]=[CH:15][C:16]3[S:22](=[O:24])(=[O:23])[CH2:21][CH2:20][C:19]([C:25]([OH:27])=[O:26])=[CH:18][C:17]=3[CH:29]=2)=[CH:30][CH:31]=1)[CH3:2]

Participants

4

Reactant 2

HCID 11430Potassium Carbonate2×HCID 22990174HCID 22990174, compound

Product 1

HCID 22990152HCID 22990152, compoundYield 37.6%

Reagents, catalysts & solvents 1

HCID 21899815MeOH tetrahydrofuranSolvent

Conditions

Temperature
65 °C

Procedure

Into a solution of methyl 7-[[4-(2-ethoxyethoxy)benzyl]oxy]-1,1-dioxo-2,3-dihydro-1-benzothiepine-4-carboxylate (0.59 g) in THF-methanol (10-5 ml) was added at room temperature a 1 M aqueous solution of potassium carbonate (2.6 ml), and the resulting mixture was stirred at 65° C. for 24 hours. Into this reaction mixture was added further a 1 M aqueous solution of potassium carbonate (1.3 ml), and the resulting mixture was stirred at 65° C. for 16 hours. After cooling to room temperature, the reaction mixture was extracted with ethyl acetate. To the aqueous layer was added 1 N hydrochloric acid (10 ml), and the resulting mixture was extracted with ethyl acetate. The organic layer was washed with an aqueous saturated solution of sodium chloride and was dried with magnesium sulfate. After concentration under reduced pressure, the precipitated crystals were collected by filtration. The crystals were washed with diisopropyl ether to obtain 7-[[4-(2-ethoxyethoxy)benzyl]oxy]-1,1-dioxo-2,3-dihydro-1-benzothiepine-4-carboxylic acid (215 mg) as light yellow crystals.

Workup

  1. stirringthe resulting mixture was stirred at 65° C. for 16 hours
  2. temperatureAfter cooling to room temperature
  3. extractionthe reaction mixture was extracted with ethyl acetate
  4. additionTo the aqueous layer was added 1 N hydrochloric acid (10 ml)
  5. extractionthe resulting mixture was extracted with ethyl acetate
  6. washThe organic layer was washed with an aqueous saturated solution of sodium chloride
  7. dry with materialwas dried with magnesium sulfate
  8. concentrationAfter concentration under reduced pressure
  9. filtrationthe precipitated crystals were collected by filtration
  10. washThe crystals were washed with diisopropyl ether

Sources & evidence

ORD record
ord-7fef42566cc74727aa5ebd8e4024e652
Source dataset
uspto-grants-2003_09
Patent number
US06627651B1

Reaction notes

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