Triethylamine → 5-(Ethylthio)carbonyloxy-1-methylpyrazol-4-yl 3-(methoxy)-2-methyl-4-(methylsulfonyl)phenyl ketone
Reaction equation
[CH3:1][O:2][C:3]1[C:4]([CH3:22])=[C:5]([C:13]([C:15]2[CH:16]=[N:17][N:18]([CH3:21])[C:19]=2[OH:20])=[O:14])[CH:6]=[CH:7][C:8]=1[S:9]([CH3:12])(=[O:11])=[O:10].C(N(CC)CC)C.[CH3:30][CH2:31][S:32][C:33](Cl)=[O:34].C(OCC)(=O)C>O1CCCC1>[CH3:1][O:2][C:3]1[C:4]([CH3:22])=[C:5]([C:13]([C:15]2[CH:16]=[N:17][N:18]([CH3:21])[C:19]=2[O:20][C:33]([S:32][CH2:31][CH3:30])=[O:34])=[O:14])[CH:6]=[CH:7][C:8]=1[S:9]([CH3:12])(=[O:10])=[O:11]Participants
6
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Procedure
To a solution of 5-hydroxy-1-methylpyrazol-4-yl 3-methoxy-2-methyl-4-(methylsulfonyl)phenyl ketone (100 mg, 0.3 mmol) in dry tetrahydrofuran (5 mL) were added triethylamine (61 mg) and 96% S-ethyl chlorothiolformate (50 mg) at room temperature. After the reaction solution was stirred for 1 hour, 150 mL of ethyl acetate was added. The mixture was washed twice with a saturated brine, the organic layer was dried over anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure. The residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=2:1) to obtain the desired product as an oil.
Workup
- washThe mixture was washed twice with a saturated brine
- dry with materialthe organic layer was dried over anhydrous sodium sulfate
- distillationthe solvent was distilled off under reduced pressure
- customThe residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=2:1)
Sources & evidence
- ORD record
- ord-018f351b31054cd0af6659a0d2a91069
- Source dataset
- uspto-grants-2011_10
- Patent number
- US08030498B2
Reaction notes
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