Methanol → Methyl 7-hydroxy-1,1-dioxo-2,3-dihydro-1-benzothiepine-4-carboxylate

HRID 1169301Notes

Reaction equation

HRID 1169301 reaction equation
[OH:1][C:2]1[CH:3]=[CH:4][C:5]2[S:11](=[O:13])(=[O:12])[CH2:10][CH2:9][C:8]([C:14]([OH:16])=[O:15])=[CH:7][C:6]=2[CH:17]=1.S(=O)(=O)(O)O.[CH3:23]O>>[OH:1][C:2]1[CH:3]=[CH:4][C:5]2[S:11](=[O:13])(=[O:12])[CH2:10][CH2:9][C:8]([C:14]([O:16][CH3:23])=[O:15])=[CH:7][C:6]=2[CH:17]=1

Participants

4

Reactant 3

HCID 887MethanolHCID 1118Sulfuric AcidHCID 229900217-Hydroxy-1,1-dioxo-2,3-dihydro-1-benzothiepine-4-carboxylic acid

Product 1

HCID 22989977Methyl 7-hydroxy-1,1-dioxo-2,3-dihydro-1-benzothiepine-4-carboxylate

Procedure

To a solution of 7-hydroxy-1,1-dioxo-2,3-dihydro-1-benzothiepine-4-carboxylic acid (856 mg) in methanol (10 ml) was added sulfuric acid (0.1 ml), and the resulting mixture was heated at reflux for 23 hours. After concentration under reduced pressure, the reaction mixture was mixed with water and was then 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 methyl 7-hydroxy-1,1-dioxo-2,3-dihydro-1-benzothiepine-4-carboxylate (848 mg) as light yellow crystals.

Workup

  1. temperaturethe resulting mixture was heated
  2. temperatureat reflux for 23 hours
  3. concentrationAfter concentration under reduced pressure
  4. additionthe reaction mixture was mixed with water
  5. extractionwas then 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-4f1045ec9a4141bfb6729f9532781bd6
Source dataset
uspto-grants-2003_09
Patent number
US06627651B1

Reaction notes

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