Hydrochloric Acid → HCID 10975989, compound

Participants

Reaction Steps

Prepared according to the general procedure from 3-benzylcyclopent-2-enone (172 mg, 1 mmol) for 24 h at 0° C. After the reaction mixture was passed though a short pad of silica gel, the resulting mixture was poured into 5 mL of a 10% HCl solution and diluted with 5 mL of Et2O. The organic layer was washed with 5 mL of a 10% HCl solution (4×) and with 5 mL of water (1×). The resulting solution was dried over MgSO4 and concentrated in vacuo to provide the title compound as a colorless oil (158 mg, 91% yield, 90% ee) after purification by flash chromatography on Iatrobeads® (2% Et2O/benzene). The physical data were identical in all respects to those previously reported (Yanagisawa et al. (1994), J. Am. Chem. Soc. 116:6130; and Moritani et al. (2000), J. Am. Chem. Soc. 122:6797 (reported an optical rotation of −96° for the (S) isomer that is 96% ee)). The enantiomeric ratio was determined by GLC using a Hydrodex-B-TBDAc (50 m×0.25 mm) column (145° C. isotherm, 1 mL/min.); (S) isomer tr=91.5 min. and (R) isomer tr=90.1 min. [α]D2=+83.9 (c=1.00, CHCl3).

Provenance & Evidence