Methanol → HCID 22990139, compound

HRID 1169513Notes

Reaction equation

HRID 1169513 reaction equation
[CH2:1]([O:3][CH2:4][CH2:5][CH2:6][C:7]1[CH:30]=[CH:29][C:10]([O:11][C:12]2[CH:13]=[CH:14][C:15]3[S:21](=[O:23])(=[O:22])[CH2:20][CH2:19][C:18]([C:24]([O:26]C)=[O:25])=[CH:17][C:16]=3[CH:28]=2)=[CH:9][CH:8]=1)[CH3:2].CO.[OH-].[Na+]>C1COCC1>[CH2:1]([O:3][CH2:4][CH2:5][CH2:6][C:7]1[CH:8]=[CH:9][C:10]([O:11][C:12]2[CH:13]=[CH:14][C:15]3[S:21](=[O:22])(=[O:23])[CH2:20][CH2:19][C:18]([C:24]([OH:26])=[O:25])=[CH:17][C:16]=3[CH:28]=2)=[CH:29][CH:30]=1)[CH3:2]

Participants

5

Reactant 3

HCID 887MethanolHCID 14798Sodium HydroxideHCID 22990155HCID 22990155, compound

Product 1

HCID 22990139HCID 22990139, compoundYield 44.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
70 °C

Procedure

To methyl 7-[4-(3-ethoxypropyl)phenoxy]-1,1-dioxo-2,3-dihydro-1-benzothiepine-4-carboxylate (0.28 g) dissolved methanol (5 ml) and THF (10 ml) was added a 1 N aqueous solution of sodium hydroxide (0.6 ml), and the resulting mixture was stirred at 70° C. for 5 hours. The reaction mixture was concentrated, was then neutralized with 1 N hydrochloric acid and was extracted with ethyl acetate. The organic layer was washed with water and an aqueous saturated solution of sodium chloride, and was dried with anhydrous magnesium sulfate. The resulting organic layer was evaporated under reduced pressure to remove the solvent to obtain 7-[4-(3-ethoxypropyl)phenoxy]-1,1-dioxo-2,3-dihydro-1-benzothiepine-4-carboxylic acid (0.12 g) as colorless crystals.

Workup

  1. concentrationThe reaction mixture was concentrated
  2. extractionwas extracted with ethyl acetate
  3. washThe organic layer was washed with water
  4. dry with materialan aqueous saturated solution of sodium chloride, and was dried with anhydrous magnesium sulfate
  5. customThe resulting organic layer was evaporated under reduced pressure
  6. customto remove the solvent

Sources & evidence

ORD record
ord-1ee57233b8d54331a449159746dc7b90
Source dataset
uspto-grants-2003_09
Patent number
US06627651B1

Reaction notes

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