Lithium hydroxide, monohydrate → 2-Ethoxy-3-[4-(2-{4-[(methanesulfonyl)oxy]phenyl}ethoxy)phenyl]propanoic acid
Reaction equation
O.[OH-].[Li+].C([O:6][C:7](=[O:33])[CH:8]([O:30][CH2:31][CH3:32])[CH2:9][C:10]1[CH:15]=[CH:14][C:13]([O:16][CH2:17][CH2:18][C:19]2[CH:24]=[CH:23][C:22]([O:25][S:26]([CH3:29])(=[O:28])=[O:27])=[CH:21][CH:20]=2)=[CH:12][CH:11]=1)C>O.O1CCCC1>[CH2:31]([O:30][CH:8]([CH2:9][C:10]1[CH:11]=[CH:12][C:13]([O:16][CH2:17][CH2:18][C:19]2[CH:20]=[CH:21][C:22]([O:25][S:26]([CH3:29])(=[O:27])=[O:28])=[CH:23][CH:24]=2)=[CH:14][CH:15]=1)[C:7]([OH:33])=[O:6])[CH3:32]Participants
5
Procedure
Lithium hydroxide hydrate (0.12 g; 2.82 mmole) dissolved in water (10 ml) was slowly added to a solution of 2-ethoxy-3-[4-(2-{4-methanesulfonyloxyphenyl}ethoxy)phenyl]propanoic acid ethyl ester (1.12 g; 2.56 mmole) in tetrahydrofuran (30 ml). After stirring at room temperature for 3 hours, water (50 ml) was added and tetrahydrofuran was removed by evaporation in vacuo. The water residue was acidified with hydrochloric acid (2 M) and extracted three times with ethyl acetate. The organic phase was dried (magnesium sulfate), filtered and the solvent was evaporated in vacuo to give 1 g (yield 96%) of 2-ethoxy-3-[4-(2-{4-methanesulfonyloxyphenyl}ethoxy)-phenyl]propanoic acid.
Workup
- customtetrahydrofuran was removed by evaporation in vacuo
- extractionextracted three times with ethyl acetate
- dry with materialThe organic phase was dried (magnesium sulfate)
- filtrationfiltered
- customthe solvent was evaporated in vacuo
Sources & evidence
- ORD record
- ord-8bf809584712432caf3e1884798f2de3
- Source dataset
- uspto-grants-2001_07
- Patent number
- US06258850B1
Reaction notes
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