Dichloromethane → 3-Chloromethyl-2-(2-methanesulfonyloxyethyl) thiophene
Reaction equation
O[CH2:2][C:3]1[CH:7]=[CH:6][S:5][C:4]=1[CH2:8][CH2:9][OH:10].[CH3:11][S:12](Cl)(=[O:14])=[O:13].C(N(C(C)C)CC)(C)C.[Cl:25]CCl>>[Cl:25][CH2:2][C:3]1[CH:7]=[CH:6][S:5][C:4]=1[CH2:8][CH2:9][O:10][S:12]([CH3:11])(=[O:14])=[O:13]Participants
5
Procedure
2.0 g of the compound obtained in Example 2 was dissolved in 35 mL of dichloromethane, and the resulting solution was cooled to below 5° C. To the solution, 3.0 g of methanesulfonyl chloride and 4.1 g of diisopropylethylamine were added, and the resulting mixture was stirred for 30 minutes. 30 mL of dichloromethane was added to the reaction solution, and the resulting mixture was washed twice with 30 mL portions of water. The organic layer was dried over anhydrous magnesium sulfate and concentrated under reduced pressure to obtain 2.9 g (yield of 91%) of the title compound as an oil.
Workup
- temperaturethe resulting solution was cooled to below 5° C
- washthe resulting mixture was washed twice with 30 mL portions of water
- dry with materialThe organic layer was dried over anhydrous magnesium sulfate
- concentrationconcentrated under reduced pressure
Sources & evidence
- ORD record
- ord-b85309a0af3f4bfbbe641ef3461e2f8d
- Source dataset
- uspto-grants-2008_11
- Patent number
- US07449580B2
Reaction notes
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