Trifluoroacetic acid → HCID 20058295, compound

HRID 2050490Notes

Reaction equation

HRID 2050490 reaction equation
[Cl-].[CH3:2][O:3][C:4]1[C:5](=[O:18])[CH:6]=[C:7]([N+:10]2[CH:15]=[CH:14][C:13]([S:16][CH3:17])=[CH:12][CH:11]=2)[O:8][CH:9]=1.FC(F)(F)C(O)=[O:22].[Cl:26]C1C=C(C=CC=1)C(OO)=O>ClCCl>[Cl-:26].[CH3:2][O:3][C:4]1[C:5](=[O:18])[CH:6]=[C:7]([N+:10]2[CH:11]=[CH:12][C:13]([S:16]([CH3:17])=[O:22])=[CH:14][CH:15]=2)[O:8][CH:9]=1

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 70297m-Chloroperbenzoic acid2×HCID 20058288HCID 20058288, compound

Product 1

HCID 20058295HCID 20058295, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Procedure

To a stirred suspension of this pyridinium chloride (1 mmol) in dichloromethane (5 ml) at 0° C. was added sufficient trifluoroacetic acid to give a clear solution. A solution of m-chloroperoxybenzoic acid (1 mmol) in dichloromethane (2 ml) was added over about 1 minute and the mixture was allowed to warm to room temperature. After 30 minutes, further m-chloroperoxybenzoic acid (1 mmol) in dichloromethane (2 ml) was added. After a further 15 minutes the solvent was removed by evaporation under reduced pressure and the residue was triturated with ethyl acetate to give 1-(5-methoxypyran-4-on-2-yl)4-methylsulphinylpyridinium chloride as a crude gum (which was used in this form for the reaction of Example 32); (DMSO-d6) 3.00(s,3H); 3.65(s,3H); 6.0(s,2H); 6.70(s,1H); 8.15(s,1H); 8.55(d,2H); 9.42(d,2H).

Workup

  1. customto give a clear solution
  2. customAfter a further 15 minutes the solvent was removed by evaporation under reduced pressure
  3. customthe residue was triturated with ethyl acetate

Sources & evidence

ORD record
ord-177a2488b3854cfdb64d755d1a30c1be
Source dataset
uspto-grants-1991_05
Patent number
US05013730

Reaction notes

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