Hydrochloric Acid → Bis(eta-cyclopentadienyl) iron

1.0 g (1.58 mmol) of the above Compound (B) (Mw 634.12) and 0.20 g (1.8 mmol) of triethylamine (available from Kishida Chemical Co., Ltd., Mw 101.6) were dissolved in chloroform, and ion-exchanged water was added thereto with the resulting mixture shaken. A chloroform phase was isolated and dried overnight over anhydrous sodium sulfate. Sodium sulfate was removed by filtration, and chloroform was distilled off under reduced pressure. The residue was then dissolved in dry dichloromethane, and 0.20 g (1.8 mmol) of distilled triethylamine (Mw 101.6) and 0.40 g (1.73 mmol) of ferrocenecarboxylic acid (available from Aldrich, Mw 230.05) were added thereto. 0.44 g (1.73 mmol) of N,N-bis(2-oxo-3-oxazolidinyl)-phosphinic chloride (Bop-Cl, available from Tokyo Kasei Kogyo Co., Ltd., Mw 254.56) was added to the reaction mixture while stirring under ice-cooling, and then stirred under ice-cooling for 30 minutes and at room temperature for 3 days. Dichloromethane was distilled off under reduced pressure to obtain a residue, which was dissolved in chloroform. A 5-weight-% aqueous sodium hydrogen carbonate solution was added thereto and shaken. An aqueous hydrochloric acid solution (pH: 4 to 5) was then added to the mixture and shaken, and ion-exchanged water was added thereto and shaken. A chloroform phase was then isolated, and dried overnight over anhydrous sodium sulfate. Sodium sulfate was removed by suction filtration, and chloroform was distilled off under reduced pressure. Chromatography with a silica gel column using a developing solvent of CHCl3 indicated that the residue contained four components, first to fourth components in the order of elution. The first and second components (unidentified) were removed, and the other components were subjected to a silica gel column chromatography using a developing solvent of CHCl3/CH3OH (10/1), to isolate the third component [ferrocene-containing, organic gelling compound (III) represented by the formula (III)]. The third component was recrystallized from hexane to obtain 0.4 g of a pale-yellow solid at a yield of 31%. The melting point of the product was 82.1 to 83.5° C. The product was identified by an FT-IR analysis. The results of the FT-IR analysis are shown in FIG. 2 and Table 1.

1. dry with materialdried overnight over anhydrous sodium sulfate
2. customSodium sulfate was removed by filtration, and chloroform
3. distillationwas distilled off under reduced pressure
4. dissolutionThe residue was then dissolved in dry dichloromethane
5. stirringwhile stirring under ice-
6. temperaturecooling
7. stirringstirred under ice-
8. distillationDichloromethane was distilled off under reduced pressure
9. customto obtain a residue, which
10. stirringshaken
11. stirringshaken
12. stirringshaken
13. dry with materialdried overnight over anhydrous sodium sulfate
14. customSodium sulfate was removed by suction filtration, and chloroform
15. distillationwas distilled off under reduced pressure
16. washfirst to fourth components in the order of elution
17. customThe first and second components (unidentified) were removed

ORD record

ord-6e648ac6605742cb8b6f42e466524262

Source dataset

uspto-grants-2006_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07041842B2