Stannous Chloride → HCID 67106249, compound

HRID 1040409Notes

Reaction equation

[OH:1][C:2]1[CH:3]=[CH:4][C:5]([N+:24]([O-])=O)=[C:6](/[CH:8]=[CH:9]/[C:10](=[O:23])[CH2:11][C:12](=[O:22])/[CH:13]=[CH:14]/[C:15]2[CH:20]=[CH:19][C:18]([OH:21])=[CH:17][CH:16]=2)[CH:7]=1.[Sn](Cl)Cl>C(OCC)(=O)C.CO.C(Cl)(Cl)Cl.C([O-])(O)=O.[Na+]>[NH2:24][C:5]1[CH:4]=[CH:3][C:2]([OH:1])=[CH:7][C:6]=1/[CH:8]=[CH:9]/[C:10](=[O:23])[CH2:11][C:12](=[O:22])/[CH:13]=[CH:14]/[C:15]1[CH:16]=[CH:17][C:18]([OH:21])=[CH:19][CH:20]=1

Participants

Conditions

Temperature: 60 °C

Procedure

To a solution of (1E,6E)-1-(5-hydroxy-2-nitrophenyl)-7-(4-hydroxyphenyl)hepta-1,6-diene-3,5-dione (26 mg, 73 μmol, synthesized in Example 4) 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=60/40 to 30/70) to obtain the title compound as a solid (6.8 mg, 37%) having the following characteristics.

Workup

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

Sources & evidence

ORD record: ord-6de507fe5be041f59beff7601abad587
Source dataset: uspto-grants-2013_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08552220B2

Reaction notes

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