Potassium Iodide → HCID 23157571, compound
Reaction equation
Cl[CH2:2][CH2:3][O:4][CH2:5][CH3:6].[CH3:7][C:8]1[CH:9]=[C:10]([SH:15])[CH:11]=[C:12]([CH3:14])[CH:13]=1.C(=O)([O-])[O-].[K+].[K+].[I-].[K+]>CN(C)C=O>[CH2:5]([O:4][CH2:3][CH2:2][S:15][C:10]1[CH:11]=[C:12]([CH3:14])[CH:13]=[C:8]([CH3:7])[CH:9]=1)[CH3:6]Participants
6
Procedure
To a solution of 1-chloro-2-ethoxyethane (5.90 mL, 54.3 mmol) and 3,5-dimethylbenzenethiol (5.00 g, 36.2 mmol) in N,N-dimethylformamide (140 mL) were added potassium carbonate (5.50 g, 39.8 mmol) and potassium iodide (0.90 g, 5.43 mmol) under stirring at room temperature, and the mixture was stirred at 80° C. for 5 hr. The reaction mixture was concentrated under reduced pressure, and water was added to the residue. The mixture was extracted with diethyl ether. The extract was dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (hexane-hexane/ethyl acetate=10/1) to give the title compound (5.80 g, yield 76%) as a colorless oil.
Workup
- stirringthe mixture was stirred at 80° C. for 5 hr
- concentrationThe reaction mixture was concentrated under reduced pressure, and water
- additionwas added to the residue
- extractionThe mixture was extracted with diethyl ether
- dry with materialThe extract was dried over anhydrous sodium sulfate
- concentrationconcentrated under reduced pressure
- customThe residue was purified by silica gel column chromatography (hexane-hexane/ethyl acetate=10/1)
Sources & evidence
- ORD record
- ord-6ebf4fee7c7f4429b6d28bee9379eac0
- Source dataset
- uspto-grants-2010_08
- Patent number
- US07786165B2
Reaction notes
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