Reaction equation
[F:1][C:2]([F:15])([F:14])[C:3]1[CH:4]=[C:5]([CH:11]=[CH:12][CH:13]=1)[CH:6]=[CH:7][C:8]([OH:10])=[O:9]>[Pd]>[F:1][C:2]([F:14])([F:15])[C:3]1[CH:4]=[C:5]([CH:11]=[CH:12][CH:13]=1)[CH2:6][CH2:7][C:8]([OH:10])=[O:9]Participants
Reactant 1
Product 1
Reagents, catalysts & solvents 1
Procedure
m-Trifluoromethyl cinnamic acid is hydrogenated at room temperature at 2 psi using palladium on carbon as catalyst to provide m-trifluoromethylbenzyl acetic acid. 21.8 Parts of this acid is dissolved in 200 parts by volume of ether. Then 100 parts by volume of 1.0 molar methyl lithium in ether is added dropwise over a 30-minute period at 0°. After the addition is complete the mixture is allowed to stir at room temperature for 3-4 hours. The mixture is poured into 1 N HCl, the organic layer is washed successively with water and 5% potassium carbonate, and then dried over anhydrous sodium sulfate. The solvent is removed to provide m-trifluoromethylbenzyl acetone. Following the procedure set out in Example 1, replacing benzyl acetone with m-trifluoromethyl benzylacetone provides racemic methyl 7-[3β-hydroxy-2β-(3(R)-hydroxy-3-methyl-5-m-trifluoromethylphenyl-1-pentyn-1-yl)-5-oxocyclopent-1α-yl]heptanoate: ##STR11## racemic methyl 7-[3β-hydroxy-2β-(3(S)-hydroxy-3-methyl-5-m-trifluoromethylphenyl-1-pentyn-1-yl)-5-oxocyclopent-1α-yl]heptanoate.
Workup
- customis hydrogenated at room temperature at 2 psi
Sources & evidence
- ORD record
- ord-8454d517b2a04de48e0277c90ccb5536
- Source dataset
- uspto-grants-1982_05
- Patent number
- US04328355
Linked notes
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