Methanol → 3-Cyclopentyl-2-(4-iodo-phenyl)-propionic acid methyl ester
Reaction equation
[CH:1]1([CH2:6][CH:7]([C:11]2[CH:16]=[CH:15][C:14]([I:17])=[CH:13][CH:12]=2)[C:8]([OH:10])=[O:9])[CH2:5][CH2:4][CH2:3][CH2:2]1.[CH3:18]O>S(=O)(=O)(O)O>[CH3:18][O:9][C:8](=[O:10])[CH:7]([C:11]1[CH:16]=[CH:15][C:14]([I:17])=[CH:13][CH:12]=1)[CH2:6][CH:1]1[CH2:5][CH2:4][CH2:3][CH2:2]1Participants
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 25 °C
Procedure
A solution of 3-cyclopentyl-2-(4-iodo-phenyl)-propionic acid (13.00 g, 37.77 mmol) in methanol (94 mL) was treated slowly with concentrated sulfuric acid (5 drops). The resulting reaction mixture was heated under reflux for 67 h. The reaction mixture was allowed to cool to 25° C. and then concentrated in vacuo to remove methanol. The residue was diluted with ethyl acetate (300 mL). The organic phase was washed with a saturated aqueous sodium chloride solution (1×100 mL), dried over sodium sulfate, filtered, and concentrated in vacuo. Flash chromatography (Merck Silica gel 60, 70-230 mesh, 100% hexanes then 19/1 hexanes/ethyl acetate) afforded 3-cyclopentyl-2-(4-iodo-phenyl)-propionic acid methyl ester (13.18 g, 97%) as a yellow semi-solid: EI-HRMS m/e calcd for C15H19IO2 (M+) 358.0430, found 358.0434.
Workup
- customThe resulting reaction mixture
- temperaturewas heated
- temperatureunder reflux for 67 h
- concentrationconcentrated in vacuo
- customto remove methanol
- additionThe residue was diluted with ethyl acetate (300 mL)
- washThe organic phase was washed with a saturated aqueous sodium chloride solution (1×100 mL)
- dry with materialdried over sodium sulfate
- filtrationfiltered
- concentrationconcentrated in vacuo
Sources & evidence
- ORD record
- ord-fcf37735cabd4c9988a7a098dcdd6602
- Source dataset
- uspto-grants-2002_05
- Patent number
- US06384220B2
Reaction notes
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