Water → HCID 136463847, compound

HRID 862096Notes

Reaction equation

HRID 862096 reaction equation
N1C=CC=CC=1.[C:7](OC(=O)C)(=[O:9])[CH3:8].[C:14]([O:18]/[N:19]=[C:20](\[C:32]1[C:37]([OH:38])=[CH:36][CH:35]=[CH:34][N:33]=1)/[C:21]1[CH:26]=[C:25]([C:27]([F:30])([F:29])[F:28])[CH:24]=[CH:23][C:22]=1[OH:31])([CH3:17])([CH3:16])[CH3:15].O>C(Cl)(Cl)Cl>[C:14]([O:18]/[N:19]=[C:20](\[C:32]1[C:37]([O:38][C:7](=[O:9])[CH3:8])=[CH:36][CH:35]=[CH:34][N:33]=1)/[C:21]1[CH:26]=[C:25]([C:27]([F:28])([F:29])[F:30])[CH:24]=[CH:23][C:22]=1[OH:31])([CH3:17])([CH3:15])[CH3:16]

Participants

6

Reactant 4

HCID 962WaterHCID 1049PyridineHCID 7918Acetic AnhydrideHCID 136463719HCID 136463719, compound

Product 1

HCID 136463847HCID 136463847, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Procedure

Pyridine (0.30 ml) was dissolved in chloroform (10 ml). To the solution was added acetic anhydride (0.18 ml), and the mixture was stirred for 50 minutes. To the reaction mixture was then added (Z)-2-(2-hydroxy-5-trifluoromethylbenzoyl)-3-hydroxypyridine O-t-butyloxime (0.21 g), and the mixture was stirred for 3 hours at room temperature. To the reaction mixture were added water and chloroform for extraction. The organic layer was dried (anhydrous magnesium sulfate), followed by distilling off the solvent under reduced pressure. The residue was purified by means of a silica gel column chromatography (eluted with ethyl acetate/hexane, then with ethyl acetate/THF) to give (Z)-3-acetoxy-2-(2-hydroxy-5-trifluoromethylbenzoyl)pyridine O-t-butyloxime (0.20 g) (Compound 46).

Workup

  1. extractionfor extraction
  2. dry with materialThe organic layer was dried (anhydrous magnesium sulfate)
  3. distillationby distilling off the solvent under reduced pressure
  4. customThe residue was purified by means of a silica gel column chromatography (
  5. washeluted with ethyl acetate/hexane

Sources & evidence

ORD record
ord-f588ea6aca9b46c28dfcf9d436055b7f
Source dataset
uspto-grants-1998_02
Patent number
US05716971

Reaction notes

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