Dimethyl Sulfoxide → 1-(3-Methoxyphenyl)-2-pyridin-4-ylethane-1,2-dione
Reaction equation
CS(C)=O.FC(F)(F)C(OC(=O)C(F)(F)F)=O.[CH3:18][O:19][C:20]1[CH:21]=[C:22]([CH:26]([OH:35])[CH:27]([C:29]2[CH:34]=[CH:33][N:32]=[CH:31][CH:30]=2)[OH:28])[CH:23]=[CH:24][CH:25]=1.C(N(CC)CC)C.C(=O)([O-])O.[Na+]>ClCCl>[CH3:18][O:19][C:20]1[CH:21]=[C:22]([C:26](=[O:35])[C:27]([C:29]2[CH:30]=[CH:31][N:32]=[CH:33][CH:34]=2)=[O:28])[CH:23]=[CH:24][CH:25]=1Participants
Reactant 5
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 0 °C
Procedure
To a stirring solution of methyl sulfoxide (11.8 g, 10.7 mL, 150 mmol) in dichloromethane (150 mL) at -78° C. was added trifluoroacetic anhydride (23.7 g, 16 mL, 113 mmol) dropwise. After ten minutes, 1-(3-methoxyphenyl)-2-pyridin-4-ylethane-1,2-diol (8.5 g, 34 mmol) in dichloromethane (60 mL) was added dropwise. After another ten minutes, triethylamine (21.3 g, 29.4 mL, 211 mmol) was added dropwise and the reaction mixture was immediately warmed to 0° C. and poured into saturated aqueous sodium hydrogen carbonate solution (300 mL). The aqueous layer was extracted with ethyl acetate (3×200 mL) and the organic layers were combined, dried over anhydrous magnesium sulfate and concentrated at reduced pressure. The resulting oil was chromatographed on silica gel eluting with 1:3 ethyl acetate:hexane to give the dione as a yellow solid (5.1 g).
Workup
- waitAfter ten minutes
- waitAfter another ten minutes
- extractionThe aqueous layer was extracted with ethyl acetate (3×200 mL)
- dry with materialdried over anhydrous magnesium sulfate
- concentrationconcentrated at reduced pressure
- customThe resulting oil was chromatographed on silica gel eluting with 1:3 ethyl acetate
Sources & evidence
- ORD record
- ord-1ff64f2b09984fcdad44407e63bd6648
- Source dataset
- uspto-grants-1998_02
- Patent number
- US05717100
Reaction notes
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