Sodium methanesulfinate → 1-(2-Methanesulfonyl-thiazol-5-yl)-propan-1-one

HRID 2067989Notes

Reaction equation

HRID 2067989 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

  1. washwashed with sat. sodium bicarbonate solution (120 ml) and brine (10 ml)
  2. extractionThe aqueous phase was extracted with ethyl acetate (2×10 mL)
  3. dry with materialThe combined organic extracts were dried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-d1220bb9608e4ee88cf24ced092964e6
Source dataset
uspto-grants-2012_10
Patent number
US08293917B2

Reaction notes

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