Hydrochloric Acid → HCID 178419209, compound

Under an argon atmosphere, a solution of cerium chloride (10.54 g, 3.0 equivalents) in THF (80 mL) was stirred at room temperature (25° C.) for 30 min. Sodium borohydride (1.67 g, 3.1 equivalents) was added, and the mixture was stirred at room temperature for 1 hr. Bis(4-methoxy-3,5-dimethylphenyl)phosphine oxide (4.54 g, 0.014 mol) synthesized in Reference Example 10 and lithium aluminum hydride (0.65 g, 1.2 equivalents) were successively added at 5° C. The mixture was stirred at room temperature for 4 hrs. Toluene (100 mL) was added at 3° C. and then 3M—HCl (40 mL) was added. The mixture was stirred at room temperature for 30 min. The reaction mixture was partitioned, and the aqueous layer was extracted with toluene (20 mL). The combined organic layer was washed with 5% aqueous NaCl solution (20 mL). The organic layer was dried over anhydrous magnesium sulfate, filtered by gravity, and the filtrate was concentrated under reduced pressure. Toluene (20 mL) and silica gel (10 g) were added to the residue and the mixture was stirred at room temperature for 10 min. The mixture was filtered by gravity, and the filtrate was concentrated under reduced pressure. The residue was recrystallized from heptane to give the title compound (3.14 g, white crystals). yield 69.6%. melting point: 81.6° C. 1H-NMR (300 MHz, CDCl3, TMS) δ: 0.37-1.56 (m, 3H), 2.27 (s, 12H), 3.72 (s, 6H), 6.13 (dq, 1H, J=377.5 Hz, 6.84 Hz), 7.27 (d, 4H, J=15.30 Hz).

1. additionwere successively added at 5° C
2. stirringThe mixture was stirred at room temperature for 4 hrs
3. stirringThe mixture was stirred at room temperature for 30 min
4. customThe reaction mixture was partitioned
5. extractionthe aqueous layer was extracted with toluene (20 mL)
6. washThe combined organic layer was washed with 5% aqueous NaCl solution (20 mL)
7. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
8. filtrationfiltered by gravity
9. concentrationthe filtrate was concentrated under reduced pressure
10. additionToluene (20 mL) and silica gel (10 g) were added to the residue
11. stirringthe mixture was stirred at room temperature for 10 min
12. filtrationThe mixture was filtered by gravity
13. concentrationthe filtrate was concentrated under reduced pressure
14. customThe residue was recrystallized from heptane

ORD record

ord-5d80587105ae48f1a9e00967538518e2

Source dataset

uspto-grants-2010_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07678942B2