Ethyl Acetate → HCID 13535401, compound

HRID 1032463Notes

Reaction equation

HRID 1032463 reaction equation
[Cl:1][C:2]1[CH:17]=[CH:16][C:5]([O:6][CH2:7][CH:8]([OH:15])[CH2:9][N:10]2[CH:14]=[N:13][CH:12]=[N:11]2)=[CH:4][CH:3]=1.CC(C)=O.OS(O)(=O)=O.O=[Cr](=O)=O.C(OCC)(=O)C.C(=O)(O)[O-].[Na+]>CC(C)=O>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([O:6][CH2:7][C:8](=[O:15])[CH2:9][N:10]2[CH:14]=[N:13][CH:12]=[N:11]2)=[CH:16][CH:17]=1

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 516892Sodium BicarbonateHCID 17806325HCID 17806325, compoundHCID 131709961Jones' reagent2×

Product 1

HCID 13535401HCID 13535401, compound

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

The 1-(4-chlorophenoxy) 3-(1,2,4-triazol-1-yl)propan-2 ol (3.0g) was dissolved in acetone (100ml) and treated with Jones reagent (3ml) for 3 h. To complete the oxidation, two subsequent additions of Jones reagent (0.5ml) were added. After cooling, ethyl acetate (150ml) was added and the reaction was neutralised by the addition of a saturated solution of sodium bicarbonate. The organic phase was separated, washed with water, dried and concentrated to dryness under reduced pressure. The residue was purified by chromatography on silica using 2% by volume methenol in chloroform as eluent, to give 1-(4-chlorophenoxy)-3-(1,2,4-triazol -1-yl)propan-2-one as a gum, NMR in deuteriochloroform: δ4.7(2H,s), 5.38(2H,s), 6.85(2H,d), 7.3(2H,d), 8.01(1H,s), 8.17(1H,s).

Workup

  1. additionwere added
  2. temperatureAfter cooling
  3. customThe organic phase was separated
  4. washwashed with water
  5. customdried
  6. concentrationconcentrated to dryness under reduced pressure
  7. customThe residue was purified by chromatography on silica using 2% by volume methenol in chloroform as eluent

Sources & evidence

ORD record
ord-7a597c39ab75403fbe3ada72f8528b32
Source dataset
uspto-grants-1990_09
Patent number
US04957934

Reaction notes

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