Sodium periodate → HCID 178458858, compound

HRID 2050407Notes

Reaction equation

HRID 2050407 reaction equation
[C:1]([C:5]1[C:6](=[O:27])[CH2:7][CH:8]([C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([O:18][C:19]3[CH:24]=[CH:23][C:22]([S:25][CH3:26])=[CH:21][CH:20]=3)[N:13]=2)[CH2:9][C:10]=1[OH:11])(=[O:4])[CH2:2][CH3:3].I([O-])(=O)(=O)=[O:29].[Na+]>CO.O>[C:1]([C:5]1[C:6](=[O:27])[CH2:7][CH:8]([C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([O:18][C:19]3[CH:20]=[CH:21][C:22]([S:25]([CH3:26])=[O:29])=[CH:23][CH:24]=3)[N:13]=2)[CH2:9][C:10]=1[OH:11])(=[O:4])[CH2:2][CH3:3]

Participants

5

Reactant 2

HCID 23667635Sodium periodateHCID 178458855HCID 178458855, compound

Product 1

HCID 178458858HCID 178458858, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

To a solution of 5.5 g (0.0143 mol) of 2-propionyl-3-hydroxy-5-(6-(4-(methylthio)phenoxy)-2-pyridyl)cyclohex-2-en-1-one in 250 mL of methanol was added a solution of 3.22 g (0.0151 mol) of sodium periodate in 25 mL of water. The resulting mixture was stirred at ambient temperature for 24 hours and the sodium iodate by-product was filtered off. The filtrate was reduced in vacuo and the residue dissolved in 150 mL of CH2Cl2 and washed with water (3×150 mL) and dried over Na2SO4 and the solvent removed in vacuo. The crude product was dissolved in CH2Cl2 and placed on a column of silica gel. The column was initially eluted with CH2Cl2 and then with a 90:10 CH2Cl2 :acetone mixture. The product fractions were combined and the solvent removed in vacuo giving the above named product in a yield of 3.2 g (56 percent of theoretical). The product melted at 78°-86° C.: Rf -0.24 (silica gel, 5:95 methanolCH2Cl2), 1H NMR (CDCl3) δ1.1 (t, 3H, CH3CH2 --), 2.5-3.6 (m, 7H, ring protons and CH3CH2 --), 2.72 (s, 3H, CH3S(O)--), 6.7-7.8 (m, 7H, ArH), 18.0 (s, 1H, OH).

Workup

  1. filtrationthe sodium iodate by-product was filtered off
  2. dissolutionthe residue dissolved in 150 mL of CH2Cl2
  3. washwashed with water (3×150 mL)
  4. dry with materialdried over Na2SO4
  5. customthe solvent removed in vacuo
  6. dissolutionThe crude product was dissolved in CH2Cl2
  7. washThe column was initially eluted with CH2Cl2
  8. customthe solvent removed in vacuo
  9. customgiving the above named product in a yield of 3.2 g (56 percent of theoretical)

Sources & evidence

ORD record
ord-5ac9242e0da3462ca011a34220a8db94
Source dataset
uspto-grants-1991_05
Patent number
US05013352

Reaction notes

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