Stannous Chloride → HCID 57567772, compound

Participants

Reaction Steps

Triisopropylsilylacetylene (12.32 grams, 67.5 mmol) and dry hexane (140 mL) were added under a dry nitrogen blanket to an oven-dried round bottom flask (1 L). Butyl lithium (2.7 M in hexane, 14.5 mL, 39.2 mmol) was added dropwise under dry nitrogen through a syringe to the mixture. After addition, the mixture was stirred at room temperature for 2 hours. This colorless solution, was then added to a suspension of 2,6-dibromoanthraquinone (5.49 grams, 15.0 mmol) in dry THF (300 mL) under dry nitrogen. The solution turned red immediately and the 2,6-dibromoanthraquininone dissolved in minutes. The mixture was stirred at room temperature overnight and the solution became dark red. When deionized (DI) water (6.0 mL) was added, the color changed to light red, and a white precipitate appeared. Tin (II) chloride (8.088 grams, 42.6 mmol) in hydrochloric acid (HCl) (18 mL, 10 weight percent) aqueous solution was then added. The mixture was heated to 60° C. for 2 hours and then cooled to room temperature. The organic solvent was removed by rotary evaporation. Deionized (DI) water (100 mL) was added and the resulting mixture was then extracted with hexane (100 mL×3). The hexane solution was washed with DI water until neutral. The washed hexane solution was concentrated and purified by column chromatography (silica gel/hexane). A bright yellow solid (8.55 grams, yield: 82%) was obtained as the product.

Provenance & Evidence