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
- 70 °C
Procedure
A solution of 3-cyclopentyl-2-(4-iodo-phenyl)-propionic acid (7.18 g, 20.86 mmol) in methanol (150 mL) was treated with a catalytic amount of concentrated sulfuric acid (7 drops). The reaction mixture was heated at 70° C. for 18 h. At this time, the reaction was cooled to 25° C. and concentrated in vacuo. The residue was partitioned between ethyl acetate (400 mL) and a saturated aqueous sodium bicarbonate solution (400 mL). The aqueous layer was extracted with ethyl acetate (1×400 mL). The combined organic extracts were washed with a saturated aqueous sodium chloride solution (1×400 mL), dried over sodium sulfate, filtered, and concentrated in vacuo to afford 3-cyclopentyl-2-(4-iodo-phenyl)-propionic acid methyl ester (7.24 g, 96.9%) as an off-white solid: mp 51-54° C.; EI-HRMS m/e calcd for C15H19IO2 (M+) 358.0429, found 358.0419.
Workup
- temperatureAt this time, the reaction was cooled to 25° C.
- concentrationconcentrated in vacuo
- customThe residue was partitioned between ethyl acetate (400 mL)
- extractionThe aqueous layer was extracted with ethyl acetate (1×400 mL)
- washThe combined organic extracts were washed with a saturated aqueous sodium chloride solution (1×400 mL)
- dry with materialdried over sodium sulfate
- filtrationfiltered
- concentrationconcentrated in vacuo
Sources & evidence
- ORD record
- ord-1690096545b74764a5a73a5b61286271
- Source dataset
- uspto-grants-2002_05
- Patent number
- US06388071B2
Reaction notes
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