Benzaldehyde → (R)-(+)-1-Phenyl-1-propanol

After stirring a mixture of (1S,2R,4R)-(7,7-dimethyl-2-morpholinobicyclo[2.2.1]heptan-1-yl)methanethiol hydrochloride (MITH•HCl; (Ib)) (58 mg, 0.20 mmol) and diethylzinc solution (3.2 mmol, 1.0 M in hexanes) at ambient temperature for 30 minutes, neat benzaldehyde (200 μL, 2.0 mmol) was added in one portion at 0° C. Upon completion of the reaction (as judged by TLC analysis), sat. aq. NH4Cl (3 mL) was slowly added to the reaction product mixture followed by ethyl acetate (20 mL). The mixture was washed twice with 1 N aq. HCl (20 mL each) and brine (5 mL), dried over solid Na2SO4, and concentrated to give a colorless oil which was purified by silica gel column chromatography (1:10 ethyl acetate/n-heptane) to give (R)-1-phenyl-propanol as a colorless oil (217 mg; 80%; 96.3% e.e.). The optical purity was determined by normal phase HPLC using a Chiralcel OD-H chiral column (eluted with isocratic IPA/Hexane=2:98, with 1.0 mL/minute flow rate; monitoring at 254 nm).

1. additionwas slowly added to the reaction product mixture
2. washThe mixture was washed twice with 1 N aq. HCl (20 mL each) and brine (5 mL)
3. dry with materialdried over solid Na2SO4
4. concentrationconcentrated
5. customto give a colorless oil which
6. customwas purified by silica gel column chromatography (1:10 ethyl acetate/n-heptane)

ORD record

ord-e318d10a42d54e039216724a7bedf1c2

Source dataset

uspto-grants-2014_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08859765B2