Sodium Iodide → HCID 69459172, compound

HRID 852382Notes

Reaction equation

HRID 852382 reaction equation
[CH2:1]([O:3][C:4](=[O:15])[CH2:5][O:6][C:7]1[CH:12]=[CH:11][C:10]([OH:13])=[CH:9][C:8]=1[CH3:14])[CH3:2].[F:16][C:17]([F:36])([F:35])[O:18][C:19]1[CH:24]=[CH:23][C:22]([C:25]#[C:26][CH2:27][CH2:28][CH2:29]OS(C)(=O)=O)=[CH:21][CH:20]=1.[Na+].[I-].C([O-])([O-])=O.[Cs+].[Cs+]>C(#N)C>[CH2:1]([O:3][C:4](=[O:15])[CH2:5][O:6][C:7]1[CH:12]=[CH:11][C:10]([O:13][CH2:29][CH2:28][CH2:27][C:26]#[C:25][C:22]2[CH:23]=[CH:24][C:19]([O:18][C:17]([F:16])([F:35])[F:36])=[CH:20][CH:21]=2)=[CH:9][C:8]=1[CH3:14])[CH3:2]

Participants

6

Reactant 4

HCID 5238Sodium IodideHCID 10796Cesium carbonateHCID 11616756Methanesulfonic acid 5-(4-trifluoromethoxy-phenyl)-pent-4-ynyl esterHCID 21986458Ethyl (4-hydroxy-2-methylphenoxy)acetate

Product 1

HCID 69459172HCID 69459172, compoundYield 63%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of 110 mg (0.52 mmol) (4-hydroxy-2-methyl-phenoxy)-acetic acid ethyl ester (WO02092590) and 169 mg (0.52 mmol) methanesulfonic acid 5-(4-trifluoromethoxy-phenyl)-pent-4-ynyl ester (example 1G]) in 5 ml acetonitrile were added 15.7 mg (0.10 mmol) NaI and 188 mg (0.58 mmol) Cs2CO3. The mixture was stirred at room temperature for 2 days and for 4.75 h at reflux. After filtration, the solvent was evaporated. The residue was redissolved in dichloromethane, dried (Na2SO4), filtered and evaporated. Purification by flash chromatography (SiO2, n-heptane/EtOAc 95:5) yielded 143 mg of the title compound as light yellow oil.

Workup

  1. temperatureat reflux
  2. filtrationAfter filtration
  3. customthe solvent was evaporated
  4. dissolutionThe residue was redissolved in dichloromethane
  5. dry with materialdried (Na2SO4)
  6. filtrationfiltered
  7. customevaporated
  8. customPurification by flash chromatography (SiO2, n-heptane/EtOAc 95:5)

Sources & evidence

ORD record
ord-c2fd30f98a014eb78c2bf06d9dc18b9e
Source dataset
uspto-grants-2007_08
Patent number
US07253192B2

Reaction notes

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