Dimethylformamide → HCID 86744130, compound

Participants

Reaction Conditions

Reaction Steps

To a stirred solution of 7.3 g (0.048 mol) of 2-(2-hydroxy-5-methylphenyl)ethanol in 30 ml of dry DMF was added 1.91 g (0.048 mol) of sodium hydride (60% in mineral oil). The mixture was stirred at room temperature until hydrogen evolution ceased, and the solution was heated at 60° C. for 30 minutes to insure complete reaction. The solution was cooled to room temperature, and to this solution was added 18.29 g of 3-(1,1-dimethylethyl)-2-phenyl-5-(toluenesulfonyloxymethyl)oxazolidine prepared by the reaction of 11.29 g (0.048 mol) of (S)-3-tert-butyl-5-hydroxymethyl-2-phenyloxazolidine with 9.15 g (0.048 mol) of p-tosylchloride. The solution was heated at 120° C. overnight. The cooled solution was poured onto 600 ml of water and this mixture was extracted with four 150 ml portions of ethyl acetate. The combined ethyl acetate extracts were washed with water, dilute sodium hydroxide solution, water, and brine. The solution was dried over sodium sulfate, filtered, and concentrated in vacuo to afford 16.1 g of crude product.

Provenance & Evidence