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

HRID 1661957Notes

Reaction equation

HRID 1661957 reaction equation
[F:1][CH:2]([F:24])[O:3][C:4]1[C:5]([CH3:23])=[C:6]([C:14]([C:16]2[CH:17]=[N:18][N:19]([CH3:22])[C:20]=2[OH:21])=[O:15])[CH:7]=[CH:8][C:9]=1[S:10]([CH3:13])(=[O:12])=[O:11].C(N(CC)CC)C.[CH3:32][CH2:33][S:34][C:35](Cl)=[O:36].C(OCC)(=O)C>O1CCCC1>[F:24][CH:2]([F:1])[O:3][C:4]1[C:5]([CH3:23])=[C:6]([C:14]([C:16]2[CH:17]=[N:18][N:19]([CH3:22])[C:20]=2[O:21][C:35]([S:34][CH2:33][CH3:32])=[O:36])=[O:15])[CH:7]=[CH:8][C:9]=1[S:10]([CH3:13])(=[O:12])=[O:11]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 8857Ethyl AcetateHCID 18056Ethyl chlorothioformateHCID 178428870HCID 178428870, compound

Product 1

HCID 872333625-(Ethylthio)carbonyloxy-1-methylpyrazol-4-yl 3-(difluoromethoxy)-2-methyl-4-(methylsulfonyl)phenyl ketone

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 5-hydroxy-1-methylpyrazol-4-yl 3-(difluoromethoxy)-2-methyl-4-(methylsulfonyl)phenyl ketone (89 mg) in dry tetrahydrofuran (5 mL) were added triethylamine (50 mg) and 96% S-ethyl chlorothiolformate (40 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

  1. washThe mixture 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=2:1)

Sources & evidence

ORD record
ord-1e4c4edabe174fce8df8b37f674b2547
Source dataset
uspto-grants-2011_10
Patent number
US08030498B2

Reaction notes

Loading…