Chlorotrimethylsilane → HCID 67287344, compound

Participants

Reaction Steps

To a suspension of lithium borohydride (71.2 mg, 3.27 mmol) in tetrahydrofuran (5 ml) was added chlorotrimethylsilane (826 μl, 6.53 mmol) at ambient temperature (exothermic reaction) and the reaction was allowed to stir for 30 minutes. 2-Methoxy-3-(2-nitrovinyl)-6-(trifluoromethyl)pyridine (193 mg, 0.778 mmol) was added, and the reaction was heated to reflux for 6 hours. The reaction was cooled to ambient temperature and quenched by the addition of 1M HCl (9 ml). After 15 minutes, the reaction was diluted with water and washed with ether and hexanes. The aqueous layer was adjust to pH 13 with 5 N aqueous sodium hydroxide and extracted with ethyl acetate (2×25 ml). The combined ethyl acetate extractions were dried over Na2SO4, filtered, and concentrated to yield the desired compound (143 mg, 0.649 mmol, 83.5% yield).

Provenance & Evidence