Tetrahydrofuran → HCID 22989975, compound

HRID 1169517Notes

Reaction equation

[CH2:1]([O:3][CH2:4][CH2:5][O:6][C:7]1[C:30]([CH3:31])=[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][C:8]=1[CH3:32])[CH3:2].C1COCC1.C(=O)([O-])[O-].[K+].[K+]>CO>[CH2:1]([O:3][CH2:4][CH2:5][O:6][C:7]1[C:8]([CH3:32])=[CH:9][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]([OH:26])=[O:25])=[CH:17][C:16]=3[CH:28]=2)=[CH:29][C:30]=1[CH3:31])[CH3:2]

Participants

Conditions

Temperature: 70 °C

Procedure

To methyl 7-[4-(2-ethoxyethoxy)-3,5-dimethylphenoxy]-1,1-dioxo-2,3-dihydro-1-benzothiepine-4-carboxylate (0.39 g) dissolved in methanol (5 ml) and THF (10 ml) was added a 1 M aqueous solution of potassium carbonate (2.5 ml), and the resulting mixture was stirred overnight at 70° C. 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-(2-ethoxyethoxy)-3,5-dimethylphenoxy]-1,1-dioxo-2,3-dihydro-1-benzothiepine-4-carboxylic acid (0.33 g) as colorless crystals.

Workup

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

Sources & evidence

ORD record: ord-bd7821a0eccc4c6c8a2c1427b0261f70
Source dataset: uspto-grants-2003_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06627651B1

Reaction notes

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