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

After stirring a mixture of (1S,2R,4R)-1,2-bis((7,7-dimethyl-2-morpholinobicyclo[2.2.1]heptan-1-yl)methyl)disulfane (IIIa) (51 mg, 0.10 mmol) and diethylzinc (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. Upon complete consumption of benzaldehyde as judged by TLC, 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 (221 mg; 81%; 95.2% e.e.).

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

ORD record

ord-c2ae099410ff41f3af2f6e5316699538

Source dataset

uspto-grants-2014_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08859765B2