Methanol → HCID 67468010, compound

HRID 509277Notes

Reaction equation

HRID 509277 reaction equation
[F:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]([O:10][CH3:11])=[O:9])=[N:6][CH:7]=1.C1C=C(Cl)C=C(C(OO)=[O:20])C=1.[O-]S([O-])(=S)=O.[Na+].[Na+].CO>C(Cl)(Cl)Cl>[F:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]([O:10][CH3:11])=[O:9])=[N+:6]([O-:20])[CH:7]=1

Participants

6

Reactant 4

HCID 887MethanolHCID 24477Sodium ThiosulfateHCID 70297m-Chloroperbenzoic acidHCID 23053520Methyl 5-fluoropyridine-2-carboxylate

Product 1

HCID 67468010HCID 67468010, compoundYield 66%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

Methyl 5-fluoropicolinate (440 mg, 2.836 mmol) was dissolved in CHCl3 (10 ml), followed by addition of mCPBA (954 mg, 4.254 mmol), and then the resulting mixture was stirred at room temperature for 15 hours. A saturated aqueous Na2S2O3 solution (15 ml) was added to the resulting reaction liquid, followed by extraction with 5% MeOH/MC (30 ml×2). The organic layer was dried over anhydrous sodium sulfate, followed by filtration and concentration, and then the residue thus obtained was subjected to MPLC (2% MeOH/MC), to obtain 318 mg of colorless oil (66%).

Workup

  1. extractionfollowed by extraction with 5% MeOH/MC (30 ml×2)
  2. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  3. filtrationfollowed by filtration and concentration
  4. customthe residue thus obtained

Sources & evidence

ORD record
ord-546e6eea78444ed68b4099f746aec07d
Source dataset
uspto-grants-2015_08
Patent number
US09096571B2

Reaction notes

Loading…