Lithium tri-s-butylborohydride → HCID 178504290, compound

To a solution of L-selectride (165 mL, 0.165 mol, 1.5 eq) in anhydrous THF (200 mL) at −78° C. was added dropwise a solution of 4-(trimethylsilyl)cyclohexanone (20 g, 0.11 mol, 1.0 eq) in anhydrous THF (100 mL). The temperature was maintained for 3 h, and then the reaction mixture was stirred at room temperature for 16 h. Then the mixture was cooled to 0° C. before being quenched with water. The resulting mixture was warmed up to room temperature, and then sodium hydroxide aqueous solution (80 mL, 3 M) was added, followed by hydrogen peroxide (80 mL, 30%). After being stirred for 3 h, the mixture was extracted with EtOAc (300 mL×3), and the combined organic layers were washed with H2O and brine, dried over Na2SO4, concentrated to give a residue which was purified by column chromatography on silica gel (petroleum ether/EtOAc=10:1) to obtain the product cis-4-(trimethylsilyl)cyclohexanol as a white solid (10.0 g, 51% yield).

1. temperatureThe temperature was maintained for 3 h
2. temperatureThen the mixture was cooled to 0° C.
3. custombefore being quenched with water
4. temperatureThe resulting mixture was warmed up to room temperature
5. additionsodium hydroxide aqueous solution (80 mL, 3 M) was added
6. stirringAfter being stirred for 3 h
7. extractionthe mixture was extracted with EtOAc (300 mL×3)
8. washthe combined organic layers were washed with H2O and brine
9. dry with materialdried over Na2SO4
10. concentrationconcentrated
11. customto give a residue which
12. customwas purified by column chromatography on silica gel (petroleum ether/EtOAc=10:1)

ORD record

ord-9abe24bea90d4cf9a4fd990109302e1e

Source dataset

uspto-grants-2016_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09340527B2