m-Chloroperbenzoic acid → 3-(2-Chloro-benzenesulfonyl)-cyclopentanecarboxylic acid methyl ester
Reaction equation
[CH3:1][O:2][C:3]([CH:5]1[CH2:9][CH2:8][CH:7](SC2C=CC=CC=2Cl)[CH2:6]1)=[O:4].[CH:18]1[CH:23]=[C:22]([Cl:24])[CH:21]=[C:20](C(OO)=O)[CH:19]=1.[S:29](=[O:32])(O)[O-:30].[Na+]>ClCCl>[CH3:1][O:2][C:3]([CH:5]1[CH2:9][CH2:8][CH:7]([S:29]([C:23]2[CH:18]=[CH:19][CH:20]=[CH:21][C:22]=2[Cl:24])(=[O:32])=[O:30])[CH2:6]1)=[O:4]Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 0 °C
Procedure
A solution of 3-(2-chloro-phenylsulfanyl)-cyclopentanecarboxylic acid methyl ester (0.24 g, 1.0 eq) in dichloromethane (10 mL) was treated at 0° C. with a solution of MCPBA (1.1 g, 5.0 eq) in dichloromethane (7 mL), which was added dropwise. The mixture was stirred at 0° C. for 3 h, then treated with 20% sodium bisulfite and stirred at RT for 15 min. The mixture was filtered, washing with chloroform. The organic phase was washed with saturated sodium bicarbonate, dried over sodium sulfate and evaporated. The residue was purified by flash chromatography on silica gel with a heptane/ethyl acetate gradient, yielding the title compound as a colorless oil (0.25 g, 90%). MS (ESI): m/z=303.2 [M+H]+.
Workup
- additionwas added dropwise
- stirringstirred at RT for 15 min
- filtrationThe mixture was filtered
- washwashing with chloroform
- washThe organic phase was washed with saturated sodium bicarbonate
- dry with materialdried over sodium sulfate
- customevaporated
- customThe residue was purified by flash chromatography on silica gel with a heptane/ethyl acetate gradient
Sources & evidence
- ORD record
- ord-bc2ad3f332d74e68afdee6e6971481d1
- Source dataset
- uspto-grants-2011_02
- Patent number
- US07893099B2
Reaction notes
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