Hydrochloric Acid → HCID 131725739, compound

Participants

Reaction Conditions

Reaction Steps

4-[2-(Trimethylsilyl)ethynyl]aniline (Takahashi et al. (1980) Synthesis, 8: 627–630) (1.0 g, 5.3 mmol) was suspended in a mixture of conc. HCl (2.4 mL) and H2O (10 mL) and cooled to 0° C. under stirring. A solution of NaNO2 (0.40 g, 5.8 nmol) in H2O (2 mL) was added while the temperature was carefully maintained between 0–5° C. After the addition was complete, the mixture was stirred for 30 min at 0° C. The resulting diazonium salt solution was then added slowly to a solution of ferrocene (0.49 g, 2.7 mmol) in toluene (100 mL) at 0° C., resulting in gas evolution. After the addition was complete, the mixture was stirred for 1 h at 0° C., warmed to rt and stirring was continued for an additional 16 h. The layers were separated and the aqueous layer was extracted with toluene (3×50 mL). The combined organic layers were washed with satd aq NaHCO3 (3×50 mL), brine (3×50 mL), dried (MgSO4) and filtered. The solvent was removed under reduced pressure and the resulting residue was purified by column chromatography (silica, CH2Cl2/hexanes, 1:1) to remove unreacted ferrocene. Elution with CH2Cl2 afforded 0.42 g (44%) of compound 3. 1H NMR δ 0.27 (s, 9H), 4.02 (s, 5H), 4.35 (A2B2, J=1.5 Hz, 2H), 4.65 (A2B2, J=1.5 Hz, 2H), 7.40 (s, 4H); 13C NMR δ 0.04, 66.5, 69.3, 69.7, 84.1, 94.0, 105.5, 120.2, 125.6, 132.0, 140.1; FAB-MS obsd 358.0851, calcd exact mass 358.0840 (C21H22FeSi).

Provenance & Evidence