Chloroform → HCID 178467845, compound

Participants

Reaction Steps

The nitro compound (315 mg; 1 m mole) in glyme (5 ml) was treated with titanium trichloride (4 m mole) in water (5 ml) under N2 with stirring at room temperature. After 2 days a further 4 m mole of TiCl3 was added and stirring was continued for 24 hrs. The product was poured into chloroform (50 ml) and saturated sodium bicarbonate was added until precipitation of titanium dioxide was complete. The two layers were filtered through `Hiflo` and the chloroform layer was washed with sodium bicarbonate solution, water and dried (sodium sulphate) to yield an oil which was chromatographed on silica to yield starting material (eluted with 5% ethyl acetate/toluene) and 4-oxopentanoyl ferrocene (30 mg; 10.6%) NMR 8, 4.75 (t, 2H); 4.44 (t, 2H); 4.21 (S, 5H); 3.1 2.6 (A2B2, 4H); 2.21 (S, 3H).

Provenance & Evidence