Hexane → HCID 58294042, compound

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%).

1. stirringThe whole was stirred under ice cooling for 1 hour and at room temperature overnight
2. extractionextracted with ethyl acetate (50 mL)
3. washThe organic layer was washed with saturated aqueous ammonium chloride solution (50 mL), saturated aqueous sodium hydrogen carbonate solution (50 mL), and brine (50 mL)
4. dry with materialdried over anhydrous magnesium sulfate
5. customThe solvent was removed in vacuo and tetrahydrofuran (30 mL), methanol (5 mL) and 1N aqueous hydrogen chloride solution (30 mL)
6. additionwere added to the residue
7. stirringthe whole was stirred at room temperature for 5 hours
8. additionThe reaction mixture was diluted with water (50 mL)
9. extractionextracted with ethyl acetate (50 mL)
10. washThe organic layer was washed with saturated aqueous sodium hydrogen carbonate solution (50 mL) and brine (50 mL)
11. dry with materialdried over anhydrous magnesium sulfate
12. customThe solvent was removed in vacuo
13. filtrationthe obtained solid was filtered off with hexane (10 mL)

ORD record

ord-8e5e9980631f425483251f9938406eae

Source dataset

uspto-grants-2012_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08088817B2