Ethyl (4-{3-[(4-fluorophenyl)sulphonyl]-4-hydroxybenzyl}-3,5-dimethylphenoxy)acetate → (4-{3-[(4-Fluorophenyl)sulphonyl]-4-hydroxybenzyl}-3,5-dimethylphenoxy)acetic acid
Reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([C:11]2[CH:12]=[C:13]([CH:30]=[CH:31][C:32]=2[OH:33])[CH2:14][C:15]2[C:27]([CH3:28])=[CH:26][C:18]([O:19][CH2:20][C:21]([O:23]CC)=[O:22])=[CH:17][C:16]=2[CH3:29])(=[O:10])=[O:9])=[CH:4][CH:3]=1>C(O)C.[OH-].[Na+]>[F:1][C:2]1[CH:3]=[CH:4][C:5]([S:8]([C:11]2[CH:12]=[C:13]([CH:30]=[CH:31][C:32]=2[OH:33])[CH2:14][C:15]2[C:27]([CH3:28])=[CH:26][C:18]([O:19][CH2:20][C:21]([OH:23])=[O:22])=[CH:17][C:16]=2[CH3:29])(=[O:10])=[O:9])=[CH:6][CH:7]=1Participants
4
Procedure
37 mg (0.08 mmol) of ethyl (4-{3-[(4-fluorophenyl)sulphonyl]-4-hydroxybenzyl}-3,5-dimethylphenoxy)acetate (Example 1) are dissolved in 1 ml of ethanol, and a few drops of 1 N aqueous sodium hydroxide solution are added. The mixture is stirred at room temperature for thirty minutes and the solvent is then removed under reduced pressure. Water is added to the residue, and the mixture is extracted three times with ethyl acetate. The combined organic phases are dried with sodium sulphate and concentrated. This gives 32 mg (90% of theory) of (4-{3-[(4-fluorophenyl)sulphonyl]-4-hydroxybenzyl}-3,5-dimethylphenoxy)acetic acid.
Workup
- customthe solvent is then removed under reduced pressure
- additionWater is added to the residue
- extractionthe mixture is extracted three times with ethyl acetate
- dry with materialThe combined organic phases are dried with sodium sulphate
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-17fe19d775f84c98ac3cd31597ce7ec0
- Source dataset
- uspto-grants-2004_08
- Patent number
- US06777442B2
Reaction notes
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