Benzyl Alcohol → HCID 70130035, compound

n-BuLi (1.6 N, 13.8 mL) was added to a solution of benzyl alcohol (2.3 mL, 22 mmol) in THF (60 mL) at −78 ° C. followed by DMSO (1.6 mL, 22 mmol). The solution was allowed to warm to room temperature and stir for 1 h. The solution was recooled to 0° C. and a solution of Pinacol (1-chloroethyl)boronate (2.06 g, 11 mmol) in THF (60 mL) was added. The solution was stirred at room temperature for 1 h and then heated at 60° C. for 5 h. The contents of the flask are poured into 0.2 N HCl (300 mL). The layers were separated and the aqueous layer was washed with ether (3×100 mL). The combined organic layers were washed with brine and dried over Na2SO4. To this solution was added (s)-pinanediol (1.87 g, 11.0 mmol) and the solution was stirred for 1 day and concentrated to yield an oil. This oil was purified by silica gel column chromatography using 10% ethyl acetate/90% hexane as an eluent. The appropriate fractions are pooled and the solvent evaporated to yield 2.66 g (77% yield) of a pale yellow oil. 1H-NMR (CDCl3) δ 7.30 (m, 5H), 4.57 (s, 2H), 4.32 (d, 1H), 3.45 (dq, 1H), 2.39-1.82 (m, 6H), 1.41 (s, 3H), 1.40 (dd, 3H), 1.29 (s, 3H), 0.84 (s, 3H).

1. customwas recooled to 0° C.
2. stirringThe solution was stirred at room temperature for 1 h
3. temperatureheated at 60° C. for 5 h
4. customThe layers were separated
5. washthe aqueous layer was washed with ether (3×100 mL)
6. washThe combined organic layers were washed with brine
7. dry with materialdried over Na2SO4
8. stirringthe solution was stirred for 1 day
9. concentrationconcentrated
10. customto yield an oil
11. customThis oil was purified by silica gel column chromatography
12. customthe solvent evaporated

ORD record

ord-4b8710c585bf40abbd2dd6ae914f0e29

Source dataset

uspto-grants-2006_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07122627B2