(S)-6-Ethyl-1,4-dioxaspiro[4.5]decane-6-propanoic Acid, 2-Hydroxyethyl Ester → (S)-6-Ethyl-alpha,alpha-diphenyl-1,4-dioxaspiro[4.5]decane-6-propanol

Participants

Reaction Steps

(S)-6-Ethyl-1,4-dioxaspiro[4.5]decane-6-propanoic acid, 2-hydroxyethyl ester (one half of the material produced in step (d), 460 g) was diluted to 1 L with anhydrous ether and added dropwise (quickly, almost as a slow stream) to a solution of phenylmagnesium bromide (5.05 mol, 1.68 L of a 3M solution) in ether at 0° C. After 5 minutes the reaction was quenched with 1M hydrochloric acid until all of the salts dissolved. The mixture was extracted with ether (3×500 mL), dried over magnesium sulfate, and concentrated to a yellow oil (175 g, some material was lost in workup).

Provenance & Evidence