Potassium Carbonate → HCID 59424218, compound

HRID 639774Notes

Reaction equation

HRID 639774 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([N:8]2[N:12]=[N:11][C:10]([CH:13]([OH:22])C(C3C=CC=CC=3)O)=[N:9]2)[CH:5]=[CH:6][CH:7]=1.C(=O)([O-])[O-].[K+].[K+].C([O-])(=O)C.[Pb+4].C([O-])(=O)C.C([O-])(=O)C.C([O-])(=O)C>C1(C)C=CC=CC=1>[Cl:1][C:2]1[CH:3]=[C:4]([N:8]2[N:12]=[N:11][C:10]([CH:13]=[O:22])=[N:9]2)[CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 594242241-[2-(3-chloro-phenyl)-2H-tetrazol-5-yl]-2-phenyl-ethane-1,2-diolHCID 178418268HCID 178418268, compound

Product 1

HCID 59424218HCID 59424218, compoundYield 68%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

1-[2-(3-chloro-phenyl)-2H-tetrazol-5-yl]-2-phenyl-ethane-1,2-diol (50.0 mg, 0.158 mmol) was weighed into a vial and toluene (3 ml) was added. Potassium carbonate (47.0 mg, 0.340 mmol) and lead (IV) acetate (70.0 mg, 0.158 mmol) were added with stirring. The reaction was allowed to stir for 2.5 hours. The reaction was filtered and ethyl acetate was added to the filtrate and an aqueous workup was done. The organic layer was washed with brine, dried over sodium sulfate, filtered and concentrated. The crude product was purified by column chromatography (40% EtOAc/Hexanes) to yield the pure product as a white solid (22.3 mg, 68%). 1H NMR (CDCl3) δ (ppm): 10.34 (s, 1H); 8.27 (s, 1H); 8.14 (m, 1H); 7.575 (d, 2H).

Workup

  1. additionwas added
  2. stirringto stir for 2.5 hours
  3. filtrationThe reaction was filtered
  4. additionethyl acetate was added to the filtrate
  5. washThe organic layer was washed with brine
  6. dry with materialdried over sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customThe crude product was purified by column chromatography (40% EtOAc/Hexanes)

Sources & evidence

ORD record
ord-ad7056fba4a445319affb906f77f1f56
Source dataset
uspto-grants-2010_04
Patent number
US07691892B2

Reaction notes

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