Hydrochloric Acid → HCID 178427273, compound

Temperature

45 °C

Under an argon atmosphere, a solution of magnesium (3.55 g, 1.0 equivalent) and a small amount of iodine in THF (30 mL) was stirred at room temperature for 1 hr. A solution of p-tolyl bromide (25 g, 0.146 mol) in THF (5 mL) was added at 30° C. The mixture was stirred at 45° C. for 30 min. and then at 5° C. for 1 hr. Diethyl phosphite (10.08 g, 0.5 equivalent) was added at 5° C. and the mixture was stirred at 5° C. for 1 hr and at room temperature (25° C.) for 30 min. Water (10 mL) was added at 3° C., and then toluene (40 mL) and 6M—HCl (20 mL) were added. The mixture was stirred at room temperature for 30 min. The reaction mixture was partitioned, and the organic layer was washed successively with water (10 mL), 5% aqueous NaHCO3 solution (10 mL) and 5% aqueous NaCl solution (10 mL). The organic layer was dried over anhydrous magnesium sulfate, filtered by gravity, and the filtrate was concentrated under reduced pressure. The residue was recrystallized from diisopropyl ether-heptane to give the title compound (7.78 g, white crystals). yield 46.3%. melting point: 93.7° C.

1. waitat 5° C. for 1 hr
2. stirringthe mixture was stirred at 5° C. for 1 hr and at room temperature (25° C.) for 30 min
3. stirringThe mixture was stirred at room temperature for 30 min
4. customThe reaction mixture was partitioned
5. washthe organic layer was washed successively with water (10 mL), 5% aqueous NaHCO3 solution (10 mL) and 5% aqueous NaCl solution (10 mL)
6. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
7. filtrationfiltered by gravity
8. concentrationthe filtrate was concentrated under reduced pressure
9. customThe residue was recrystallized from diisopropyl ether-heptane

ORD record

ord-a435382ae94b4d9ca484b6e8d0fd51f6

Source dataset

uspto-grants-2010_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07678942B2