Lithium Hydroxide → 3-Cyclopentyl-2-[4-(3-hydroxy-prop-1-ynyl)-phenyl]-propionic acid
Reaction equation
C[O:2][C:3](=[O:21])[CH:4]([C:11]1[CH:16]=[CH:15][C:14]([C:17]#[C:18][CH2:19][OH:20])=[CH:13][CH:12]=1)[CH2:5][CH:6]1[CH2:10][CH2:9][CH2:8][CH2:7]1.[OH-].[Li+]>CO.O>[CH:6]1([CH2:5][CH:4]([C:11]2[CH:16]=[CH:15][C:14]([C:17]#[C:18][CH2:19][OH:20])=[CH:13][CH:12]=2)[C:3]([OH:21])=[O:2])[CH2:10][CH2:9][CH2:8][CH2:7]1Participants
Reactant 2
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 25 °C
Procedure
A solution of 3-cyclopentyl-2-[4-(3-hydroxy-prop-1-ynyl)-phenyl]-propionic acid methyl ester (1.55 g, 5.41 mmol) in methanol (30 mL) and water (30 mL) was treated with lithium hydroxide (2.60 g, 61.9 mmol). The reaction mixture was stirred at 25° C. for 48 h. At this time, the reaction was concentrated in vacuo. The residue was re-dissolved in water (100 mL) which was then acidified to pH=2 with concentrated hydrochloric acid. This solution was extracted with ethyl acetate (2×120 mL). The combined organic extracts were then washed with a half-saturated aqueous sodium chloride solution (1×40 mL), dried over sodium sulfate, filtered, and concentrated in vacuo to afford 3-cyclopentyl-2-[4-(3-hydroxy-prop-1-ynyl)-phenyl]-propionic acid (1.27 g, 86%) as an off-white solid.
Workup
- concentrationAt this time, the reaction was concentrated in vacuo
- dissolutionThe residue was re-dissolved in water (100 mL) which
- extractionThis solution was extracted with ethyl acetate (2×120 mL)
- washThe combined organic extracts were then washed with a half-saturated aqueous sodium chloride solution (1×40 mL)
- dry with materialdried over sodium sulfate
- filtrationfiltered
- concentrationconcentrated in vacuo
Sources & evidence
- ORD record
- ord-004f7fc66ee248b98fe8682e6ba655a5
- Source dataset
- uspto-grants-2002_05
- Patent number
- US06388071B2
Reaction notes
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