Acetic Anhydride → HCID 71534205, compound

Participants

Reaction Steps

To a solution of the tetralone obtained in Step C (350 mg, 1.0 mmol) in isopropanol (10 mL) at ambient temperature there is added sodium borohydride (190 mg, 5.0 mmol). The mixture is stirred at reflux overnight and then a solution of sodium hydroxide (80 mg, 2.0 mmol) in water (2.0 mL) is added dropwise. The mixture is maintained under reflux for 30 minutes, and then acetone (1.5 mL) is added. After 10 minutes, the mixture is cooled to ambient temperature before being concentrated under reduced pressure. The oil thereby obtained is dissolved in dichloromethane (10 mL). Dimethylaminopyridine (270 mg, 2.2 mmol) is then added, followed by acetic anhydride (210 μL, 2.2 mmol) dropwise. The solution is stirred at ambient temperature for 1 hour and then water is added. The pH of the solution is adjusted to from 8 to 9 by adding saturated sodium hydrogen carbonate solution. The aqueous phase is extracted with dichloromethane and the organic phases are washed with saturated NaCl solution, dried over magnesium sulphate, filtered and evaporated. The title compound is obtained after purification by flash column chromatography (ethyl acetate-petroleum ether: 90-10, then ethyl acetate-methanol: 90-10) in the form of an oil in a yield of 79%.

Provenance & Evidence