Potassium Carbonate → HCID 22990176, compound

HRID 1169453Notes

Reaction equation

HRID 1169453 reaction equation
[CH2:1]([O:3][CH2:4][CH2:5][O:6][C:7]1[CH:31]=[CH:30][CH:29]=[CH:28][C:8]=1[CH2:9][O:10][C:11]1[CH:12]=[CH:13][C:14]2[S:20](=[O:22])(=[O:21])[CH2:19][CH2:18][C:17]([C:23]([O:25]C)=[O:24])=[CH:16][C:15]=2[CH:27]=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:31]=[CH:30][CH:29]=[CH:28][C:8]=1[CH2:9][O:10][C:11]1[CH:12]=[CH:13][C:14]2[S:20](=[O:22])(=[O:21])[CH2:19][CH2:18][C:17]([C:23]([OH:25])=[O:24])=[CH:16][C:15]=2[CH:27]=1)[CH3:2]

Participants

4

Reactant 2

HCID 11430Potassium CarbonateHCID 22990000HCID 22990000, compound

Product 1

HCID 22990176HCID 22990176, compoundYield 62.1%

Reagents, catalysts & solvents 1

HCID 21899815MeOH tetrahydrofuranSolvent

Conditions

Temperature
60 °C

Procedure

Into a solution of methyl 7-[[2-(2-ethoxyethoxy)benzyl]oxy]-1,1-dioxo-2,3-dihydro-1-benzothiepine-4-carboxylate (0.64 g) in THF-methanol (6-3 ml) was added at room temperature a 1 M aqueous solution of potassium carbonate (2.9 ml), and the resulting mixture was stirred at 60° C. for 20 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-[[2-(2-ethoxyethoxy)benzyl]oxy]-1,1-dioxo-2,3-dihydro-1-benzothiepine-4-carboxylic acid (385 mg) as light yellow crystals.

Workup

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

Sources & evidence

ORD record
ord-cfc9f2d1a5de4a9da4046ab85168fa49
Source dataset
uspto-grants-2003_09
Patent number
US06627651B1

Reaction notes

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