Hydrochloric Acid → 2-(3-Oxo-cyclohexyl)-malonic acid dibenzyl ester

Participants

Reaction Steps

To a solution of LiAlH4 (6 mL, 6 mmol) under N2 at 0° C. was added a solution of (S)-1,1′-binaphthol (3.43 g, 12 mmol) in THF (48 mL) and stirred for 30 min. The reaction was warmed to RT. To this was added a solution of sodium salt benzyl malonate in THF which was prepared by reacting benzyl malonate (14.99 mL, 60 mmol), NaH (60% by wt., 0.216 g, 5.4 mmol), and THF (60 mL) until all bubbling ceased. Next, cyclohexenone (5.82 mL, 60 mmol) and dibenzlmalonate (1.35 mL, 5.4 mmol) were added and the reaction mixture was stirred overnight. 1.0 N HCl was added and extracted with EtOAc (3×). The combined EtOAc layers were washed (brine), dried (MgSO4), filtered, and concentrated. Flash chromatography (silica gel, acetone/hexanes gradient) gave the title compound (16.17 g, 71%). Mass Spectrum (FIA) (m/z) 381.3 [M+1].

Provenance & Evidence