Triacetoxyperiodinane → HCID 11338407, compound

HRID 1796334Notes

Reaction equation

HRID 1796334 reaction equation
[CH3:1][C:2]1[N:7]=[C:6]([NH:8][C:9]2[C:14]([CH3:15])=[CH:13][C:12]([CH3:16])=[CH:11][C:10]=2[CH3:17])[C:5]([S:18]([C:21]2[CH:26]=[CH:25][C:24]([CH2:27][OH:28])=[CH:23][CH:22]=2)(=[O:20])=[O:19])=[CH:4][CH:3]=1.CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O>C(Cl)(Cl)Cl.CCOC(C)=O>[CH3:1][C:2]1[N:7]=[C:6]([NH:8][C:9]2[C:14]([CH3:15])=[CH:13][C:12]([CH3:16])=[CH:11][C:10]=2[CH3:17])[C:5]([S:18]([C:21]2[CH:22]=[CH:23][C:24]([CH:27]=[O:28])=[CH:25][CH:26]=2)(=[O:20])=[O:19])=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 159087TriacetoxyperiodinaneHCID 11395370HCID 11395370, compound

Product 1

HCID 11338407HCID 11338407, compoundYield 95%

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
25 °C

Procedure

{4-[6-Methyl-2-(2,4,6-trimethylphenylamino)-pyridine-3-sulfonyl]-phenyl}-methanol, prepared as described in Example 50, (0.5 g, 1.26 mmol) was dissolved in CHCl3 (10 mL) and Dess-Martin periodinane (0.59 g, 1.39 mmol) was added. The reaction was stirred at 25° C. for 16 h, dissolved in EtOAc (100 mL), and the EtOAc was washed with sat sodium thiosulfate solution (20 mL), water (20 mL) and brine, dried and stripped in vacuo. The residue was chromatographed on silica gel using 20% EtOAc/hexanes eluent to give 4-[6-methyl-2-(2,4,6-trimethylphenylamino)-pyridine-3-sulfonyl]-benzaldehyde (472 mg, 95% yield) as an amorphous solid. mass spec. (AP+): m/z 395 (M+1).

Workup

  1. washthe EtOAc was washed with sat sodium thiosulfate solution (20 mL), water (20 mL) and brine
  2. customdried
  3. customThe residue was chromatographed on silica gel using 20% EtOAc/hexanes eluent

Sources & evidence

ORD record
ord-a52d7e17f91a48368d2e5bd23b4b7f31
Source dataset
uspto-grants-2006_04
Patent number
US07030145B2

Reaction notes

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