Ethyl Acetate → HCID 17862393, compound

HRID 644907Notes

Reaction equation

HRID 644907 reaction equation
[CH2:1]([NH:4][C:5]([N:7]1[C:11]([CH3:12])=[CH:10][C:9]([O:13][C:14]2[C:19]([Cl:20])=[CH:18][C:17]([C:21]([F:24])([F:23])[F:22])=[CH:16][C:15]=2[Cl:25])=[N:8]1)=[O:6])[CH:2]=C.I([O-])(=O)(=O)=[O:27].[Na+].S([O-])([O-])(=O)=S.[Na+].[Na+].C(OCC)(=O)C>CCOCC.O.[Os](=O)(=O)(=O)=O>[CH:2]([CH2:1][NH:4][C:5]([N:7]1[C:11]([CH3:12])=[CH:10][C:9]([O:13][C:14]2[C:19]([Cl:20])=[CH:18][C:17]([C:21]([F:22])([F:23])[F:24])=[CH:16][C:15]=2[Cl:25])=[N:8]1)=[O:6])=[O:27]

Participants

8

Reactant 4

HCID 8857Ethyl AcetateHCID 24477Sodium ThiosulfateHCID 17862413HCID 17862413, compoundHCID 23667635Sodium periodate

Product 1

HCID 17862393HCID 17862393, compoundYield 49.1%

Reagents, catalysts & solvents 3

HCID 30318Osmium TetroxideCatalystHCID 962WaterSolventHCID 3283Diethyl EtherSolvent

Procedure

N-allyl-3-(2,6-dichloro-4-trifluoromethylphenyloxy)-5-methylpyrazole-1-carboxamide (4.3 g, 10.9 mmol) was dissolved in a solution mixture of ether (50 ml) and water (50 ml), an aqueous solution (60 ml) of osmium tetraoxide (254 mg, 1.0 mmol) and sodium periodate (4.7 g, 21.8 mmol) were added, and the mixture was stirred at room temperature overnight. After completion of the reaction, a 10% sodium thiosulfate aqueous solution (100 ml) and ethyl acetate (100 ml) were added to the reaction solution, and an organic layer was separated and an aqueous layer was extracted with ethyl acetate (50 ml×2). These organic layers combined were washed with a saturated sodium chloride aqueous solution, dried over anhydrous magnesium sulfate and filtered to remove a desiccant. The solvent was distilled off from the filtrate under reduced pressure. The resultant crude product was purified with a silica gel column (ethyl acetate/hexane=1/7→1/5), to give a white solid of N-formylmethyl-3-(2,6-dichloro-4-trifluoromethylphenyloxy)-5-methylpyrazole-1-carboxamide (2.12 g, yield: 49.1%). mp: 111-113° C.; 1H-NMR (CDCl3, TMS, ppm): δ 2.59 (d, J=0.8 Hz, 3H), 4.17 (d, J=5.5 Hz, 2H), 5.81 (q, J=0.8 Hz, 1H), 7.21 (br t, J=5.5 Hz, 1H), 7.67 (s, 2H), 9.66 (s, 1H).

Workup

  1. customAfter completion of the reaction
  2. customan organic layer was separated
  3. extractionan aqueous layer was extracted with ethyl acetate (50 ml×2)
  4. washThese organic layers combined were washed with a saturated sodium chloride aqueous solution
  5. dry with materialdried over anhydrous magnesium sulfate
  6. filtrationfiltered
  7. customto remove a desiccant
  8. distillationThe solvent was distilled off from the filtrate under reduced pressure
  9. customThe resultant crude product was purified with a silica gel column (ethyl acetate/hexane=1/7→1/5)

Sources & evidence

ORD record
ord-232b5e5fd90448838d4fcc8a1e1f3463
Source dataset
uspto-grants-2010_04
Patent number
US07700786B2

Reaction notes

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