Sodium methanesulfinate → 1-(2-Methanesulfonyl-thiazol-5-yl)-propan-1-one
Reaction equation
Br[C:2]1[S:3][C:4]([C:7](=[O:10])[CH2:8][CH3:9])=[CH:5][N:6]=1.[CH3:11][S:12]([O-:14])=[O:13].[Na+]>CS(C)=O.C(OCC)(=O)C.[Cu](I)I>[CH3:11][S:12]([C:2]1[S:3][C:4]([C:7](=[O:10])[CH2:8][CH3:9])=[CH:5][N:6]=1)(=[O:14])=[O:13]Participants
6
Conditions
- Temperature
- 120 °C
Procedure
To a solution of 1-(2-bromo-thiazol-5-yl)-propan-1-one (75 mg, 0.34 mmol) in dimethyl sulfoxide (3 mL) was added the sodium methylsulfinate (41 mg, 0.34 mmol) followed by copper iodide (65 mg, 0.34 mmol). The mixture was heated in a microwave at 120° C. for 1 h. The reaction was diluted with ethyl acetate (20 mL) and washed with sat. sodium bicarbonate solution (120 ml) and brine (10 ml). The aqueous phase was extracted with ethyl acetate (2×10 mL). The combined organic extracts were dried over magnesium sulfate, filtered and concentrated to give 1-(2-methanesulfonyl-thiazol-5-yl)-propan-1-one (42 mg, 56%) that was used without further purification.
Workup
- washwashed with sat. sodium bicarbonate solution (120 ml) and brine (10 ml)
- extractionThe aqueous phase was extracted with ethyl acetate (2×10 mL)
- dry with materialThe combined organic extracts were dried over magnesium sulfate
- filtrationfiltered
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-d1220bb9608e4ee88cf24ced092964e6
- Source dataset
- uspto-grants-2012_10
- Patent number
- US08293917B2
Reaction notes
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