Tetrahydrofuran → (3-Chloro-4-methylsulfanyl-phenyl)-acetic acid ethyl ester
Reaction equation
[CH2:1]([O:3][C:4](=[O:19])[CH:5](OC(=O)C)[C:6]1[CH:11]=[CH:10][C:9]([S:12][CH3:13])=[C:8]([Cl:14])[CH:7]=1)[CH3:2].[I-].[Sm+3].[I-].[I-].O1CCCC1>CN(C)P(N(C)C)(N(C)C)=O.CO.O>[CH2:1]([O:3][C:4](=[O:19])[CH2:5][C:6]1[CH:11]=[CH:10][C:9]([S:12][CH3:13])=[C:8]([Cl:14])[CH:7]=1)[CH3:2]Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 3
Conditions
- Temperature
- 25 °C
Procedure
A solution of acetoxy-(3-chloro-4-methylsulfanyl-phenyl)-acetic acid ethyl ester (1.47 g, 4.87 mmol) in hexamethylphosphoramide (7.2 mL) and methanol (20 μL) was treated with a 0.1M solution of samarium iodide in tetrahydrofuran (146 mL, 14.6 mmol). The reaction mixture was stirred at 25° C. under nitrogen for 6 min. During this time period, the reaction mixture changed from purple to white. The reaction mixture was diluted with water (150 mL) and then extracted with methylene chloride (3×100 mL). The combined organic layers were dried over sodium sulfate, filtered, and concentrated in vacuo. Flash chromatography (Merck Silica gel 60, 230–400 mesh, 4/1 hexanes/ethyl acetate) afforded (3-chloro-4-methylsulfanyl-phenyl)-acetic acid ethyl ester (0.71 g, 60%) as a light yellow oil: EI-HRMS m/e calcd for C11H13ClO2S (M+) 244.0324, found 244.0332.
Workup
- extractionextracted with methylene chloride (3×100 mL)
- dry with materialThe combined organic layers were dried over sodium sulfate
- filtrationfiltered
- concentrationconcentrated in vacuo
Sources & evidence
- ORD record
- ord-12844526e928404cb7b23bc1979f5ab9
- Source dataset
- uspto-grants-2007_05
- Patent number
- US07223868B2
Reaction notes
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