HCID 129792804, compound → HCID 178520603, compound

Participants

Reaction Conditions

Reaction Steps

One gram of 2-ferrocenyl-2-(3-hydroxypropyl)tetrahydrofuran (II) was dissloved in 10 ml of trifluoroacetic acid at 25°C for 2 hours. The trifluoroacetic acid was removed under reduced pressure at 25°C and ferrocene, 5.41 g (0.032 mole), dissolved in 25 ml of methylene chloride, was added to the residue. The solution was stirred 40 hours at 25°C and then treated with 50 ml of H2O and enough ascorbic acid solution (drop by drop) to reduce the ferricinium ion present. The phases were separated and the aqueous phase was extracted with 25 ml of methylene chloride. The methylene chloride phases were combined and dried over calcium chloride. The solvent (CH2Cl2) was removed under reduced pressure and the residue was heated at 175°/0.25 mm pressure of 15 minutes to remove residual unreacted ferrocene. The nonvolatile residue was then dissolved in a 2% methyl alcohol in ethyl acetate solution and chromatographed on a dry 3.6 cm by 25 cm alumina column. Extraction of the major yellow band with methyl alcohol gave 1.1 g (69% yield) of 4,4-diferrocenylheptane-1,7-diol (IV). Recrystallization from benzene gave a mp of 168°-171°C. An additional recrystallization from methyl alcohol gave a mp of 169°-171°C.

Provenance & Evidence