Triethylamine → 5-(Ethylthio)carbonyloxy-1-methylpyrazol-4-yl 2-methyl-4-(methylsulfonyl)-3-(4,5-dihydroisoxazol-3-yl)phenyl ketone

HRID 1661955Notes

Reaction equation

HRID 1661955 reaction equation
[O:1]1[CH2:5][CH2:4][C:3]([C:6]2[C:7]([CH3:25])=[C:8]([C:16]([C:18]3[CH:19]=[N:20][N:21]([CH3:24])[C:22]=3[OH:23])=[O:17])[CH:9]=[CH:10][C:11]=2[S:12]([CH3:15])(=[O:14])=[O:13])=[N:2]1.C(N(CC)CC)C.[CH3:33][CH2:34][S:35][C:36](Cl)=[O:37].C(OCC)(=O)C>O1CCCC1>[CH3:25][C:7]1[C:6]([C:3]2[CH2:4][CH2:5][O:1][N:2]=2)=[C:11]([S:12]([CH3:15])(=[O:14])=[O:13])[CH:10]=[CH:9][C:8]=1[C:16]([C:18]1[CH:19]=[N:20][N:21]([CH3:24])[C:22]=1[O:23][C:36]([S:35][CH2:34][CH3:33])=[O:37])=[O:17]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 8857Ethyl AcetateHCID 18056Ethyl chlorothioformateHCID 178428868HCID 178428868, compound

Product 1

HCID 872334215-(Ethylthio)carbonyloxy-1-methylpyrazol-4-yl 2-methyl-4-(methylsulfonyl)-3-(4,5-dihydroisoxazol-3-yl)phenyl ketoneYield 66%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 5-hydroxy-1-methylpyrazol-4-yl 3-(4,5-dihydroisoxazol-3-yl)-2-methyl-4-(methylsulfonyl)phenyl ketone (100 mg, 2.75×10−4 mol) in anhydrous tetrahydrofuran (5 mL) were added triethylamine (55 mg) and 96% S-ethyl chlorothiolformate (45 mg) at room temperature. After the reaction solution was stirred for 1 hour, 150 mL of ethyl acetate was added, and the solution 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=6:4) to obtain the desired product (82 mg) as an oil.

Workup

  1. washthe solution was washed twice with a saturated brine
  2. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  3. distillationthe solvent was distilled off under reduced pressure
  4. customThe residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=6:4)

Sources & evidence

ORD record
ord-394a26a839924ab6a43d876ad922d091
Source dataset
uspto-grants-2011_10
Patent number
US08030498B2

Reaction notes

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