Potassium tert-butoxide → HCID 18968199, compound

Participants

Reaction Steps

Potassium tert-butoxide (27.5 mg, 0.25 mmol) was added to a solution of methyl (S)-4-cyano-4-(3,4-dimethoxyphenyl)-5-methylhexanoate (150 mg, 0.491 mmol; 97% ee by chiral HPLC analysis) in anhydrous dimethyl sulphoxide (4 ml). The resulting golden yellow solution was stirred at room temperature for five minutes and then heated at 100° C. for 1 hour. The reaction mixture was then worked up by quenching with acetic acid and evaporation of solvent under high vacuum, followed by partitioning of the residue between methyl tert-butyl ether and water. The washed and dried organic extract was concentrated to provide methyl 4-cyano-4-(3,4-dimethoxyphenyl)-5-methylhexanoate as an oil (60 mg; 40% recovery). Chiral HPLC analysis of a sample removed prior to heating the reaction mixture at 100° C. showed methyl (S)-4-cyano-4-(3,4-dimethoxyphenyl)-5-methylhexanoate of substantially reduced enantiomeric purity (ca. 10% ee).

Provenance & Evidence