Hydrochloric Acid → HCID 12938740, compound

Temperature

-10 °C

Enantioselective crotylation of dihydrocinnamaldehyde to give (3S,4S)-4-Methyl-1-phenyl-hex-5-en-3-ol: To a cooled (−10° C.) solution of (4R,5R)-2-((cis)-but-2-enyl)-2-chloro-3,4-dimethyl-5-phenyl-[1,3,2]oxazasilolidine (0.431 g, 1.5 mmol) in toluene (2.5 mL) was added dihydrocinnamaldehyde (0.132 mL, 1.0 mmol). The reaction mixture was allowed to stir for 12 hours at −10° C. To this solution was added 1N HCl (4 mL) and EtOAc (4 mL) and the mixture was stirred for 10 min. The layers were separated and the aqueous layer was extracted with EtOAc (3×5 mL). The combined organics were dried over MgSO4, filtered, and concentrated. HPLC analysis of the residue at this stage revealed a syn:anti diastereoselectivity of 10:1, and an enantiomeric excess for the major syn product of 81%. The residue was purified by chromatography on silica gel to afford 0.116 g (61%) of (3S,4S)-4-Methyl-1-phenyl-hex-5-en-3-ol (81% ee).

1. stirringthe mixture was stirred for 10 min
2. customThe layers were separated
3. extractionthe aqueous layer was extracted with EtOAc (3×5 mL)
4. dry with materialThe combined organics were dried over MgSO4
5. filtrationfiltered
6. concentrationconcentrated
7. customThe residue was purified by chromatography on silica gel

ORD record

ord-b236654be17a422d88ec4427182b65fc

Source dataset

uspto-grants-2009_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07534905B2