Hexane → HCID 58294042, compound

Participants

Reaction Steps

1.6 M n-Butyllithium in hexane solution (4.7 mL, 7.6 mmol) was added dropwise to a solution of 2-[3-bromo-2-(2-bromoethoxy)-5-chlorophenyl]-2,5,5-trimethyl-1,3-dioxane (Reference compound No. 5-1, 2.8 g, 6.3 mmol) in anhydrous tetrahydrofuran (30 mL) over 5 minutes at −70° C. and the whole was stirred for 1.5 hours. The whole was stirred under ice cooling for 1 hour and at room temperature overnight. The reaction mixture was diluted with water (50 mL) and extracted with ethyl acetate (50 mL). The organic layer was washed with saturated aqueous ammonium chloride solution (50 mL), saturated aqueous sodium hydrogen carbonate solution (50 mL), and brine (50 mL), and then dried over anhydrous magnesium sulfate. The solvent was removed in vacuo and tetrahydrofuran (30 mL), methanol (5 mL) and 1N aqueous hydrogen chloride solution (30 mL) were added to the residue, and the whole was stirred at room temperature for 5 hours. The reaction mixture was diluted with water (50 mL) and extracted with ethyl acetate (50 mL). The organic layer was washed with saturated aqueous sodium hydrogen carbonate solution (50 mL) and brine (50 mL), and then dried over anhydrous magnesium sulfate. The solvent was removed in vacuo and the obtained solid was filtered off with hexane (10 mL) to give the title reference compound (0.31 g) as a pale yellow solid (Yield 25%).

Provenance & Evidence