Tetrahydrofuran → HCID 86615002, compound

HRID 732417Notes

Reaction equation

HRID 732417 reaction equation
[S:1]([O-:6])(O[O-])(=O)=[O:2].[K+].[K+].[CH3:9][O:10][C:11](=[O:23])[C:12]1[CH:17]=[C:16](SCCC)[N:15]=[C:14]([Cl:22])[CH:13]=1.[CH2:24]1[CH2:28]OC[CH2:25]1>O.CO>[CH3:9][O:10][C:11](=[O:23])[C:12]1[CH:17]=[C:16]([S:1]([CH2:25][CH2:24][CH3:28])(=[O:6])=[O:2])[N:15]=[C:14]([Cl:22])[CH:13]=1

Participants

6

Reactant 3

HCID 8028TetrahydrofuranHCID 10313463Potassium peroxymonosulphateHCID 86081340HCID 86081340, compound

Product 1

HCID 86615002HCID 86615002, compoundYield 52%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent2×

Procedure

Add a suspension of potassium peroxymonosulfate (35.6 g, 57.7 mmol) in water (80 mL) to a cooled solution of 2-chloro-6-propylsulfanyl-isonicotinic acid methyl ester (4.71 g, 19.2 mmol) in methanol (40 mL) and THF (40 mL). Stir the mixture at room temperature for 3 days. Dilute the mixture with water and extract with dichloromethane (3×100 mL). Wash the combined extracts with water, dry (magnesium sulfate), concentrate and purify (silica gel chromatography, eluting with 20:80 ethyl acetate:hexanes) to give the title product (2.75 g, 52%).

Workup

  1. additionAdd
  2. extractionextract with dichloromethane (3×100 mL)
  3. washWash the combined extracts with water
  4. dry with materialdry (magnesium sulfate)
  5. concentrationconcentrate
  6. custompurify
  7. wash(silica gel chromatography, eluting with 20:80 ethyl acetate:hexanes)

Sources & evidence

ORD record
ord-84cb12cdba574481a796bebd39d19e89
Source dataset
uspto-grants-2009_09
Patent number
US07585885B2

Reaction notes

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