Stannous Chloride → HCID 68554856, compound

HRID 1854695Notes

Reaction equation

HRID 1854695 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5](/[CH:8]=[CH:9]/[C:10](=[O:25])[CH2:11][C:12](=[O:24])/[CH:13]=[CH:14]/[C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=2[N+:21]([O-])=O)=[CH:4][CH:3]=1.[Sn](Cl)Cl>C(OCC)(=O)C.CO.C(Cl)(Cl)Cl.C([O-])(O)=O.[Na+]>[NH2:21][C:16]1[CH:17]=[CH:18][CH:19]=[CH:20][C:15]=1/[CH:14]=[CH:13]/[C:12](=[O:24])[CH2:11][C:10](=[O:25])/[CH:9]=[CH:8]/[C:5]1[CH:4]=[CH:3][C:2]([OH:1])=[CH:7][CH:6]=1

Participants

6

Reactant 2

HCID 24479Stannous ChlorideHCID 67107578HCID 67107578, compound

Product 1

HCID 68554856HCID 68554856, compoundYield 46.5%

Reagents, catalysts & solvents 3

HCID 8857Ethyl AcetateSolventHCID 516892Sodium BicarbonateSolventHCID 21584188Chloroform methanolSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of (1E,6E)-1-(4-hydroxyphenyl)-7-(2-nitrophenyl)hepta-1,6-diene-3,5-dione (26 mg, 77 μmol, synthesized in Example 344) in 3.0 mL of ethyl acetate was added anhydrous tin(II) chloride (57 mg, 0.30 mmol) at room temperature. After being stirred at 60° C. for 1.5 h, the reaction mixture was cooled to room temperature, and was diluted with 10% methanol/chloroform and saturated NaHCO3 aqueous solution, successively. The mixture was shaken before filtration to remove inorganic salts. The organic layer after separation was washed with brine, and dried over MgSO4. After filtration, the filtrate was concentrated in vacuo, and the residue was purified by silica gel column chromatography (hexane/ethyl acetate=70/30 to 60/40) to obtain the title compound as a solid (11.0 mg, 46%) having the following characteristics.

Workup

  1. temperaturethe reaction mixture was cooled to room temperature
  2. stirringThe mixture was shaken before filtration
  3. customto remove inorganic salts
  4. customThe organic layer after separation
  5. washwas washed with brine
  6. dry with materialdried over MgSO4
  7. filtrationAfter filtration
  8. concentrationthe filtrate was concentrated in vacuo
  9. customthe residue was purified by silica gel column chromatography (hexane/ethyl acetate=70/30 to 60/40)

Sources & evidence

ORD record
ord-e2399be268754f4baf3bb978bf450f02
Source dataset
uspto-grants-2015_02
Patent number
US08962674B2

Reaction notes

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