tert-Butanol → HCID 21837517, compound

Participants

Reaction Conditions

Reaction Steps

At room temperature, 9.0 ml (64.4 mmol) of triethylamine, then 13.9 ml (64.4 mmol) of diphenylphosphoryl azide are added to 10 g (51.5 mmol) of thiochroman-8-carboxylic acid in 260 ml of toluene. The whole is heated at 90° C. for 2 hours, then 4.8 g (64.4 mmol) of tert-butanol dissolved in 10 ml of toluene are added dropwise and the temperature is subsequently maintained at 90° C. for a further 20 hours. The whole is allowed to cool and washed with 120 ml of water, 120 ml of 0.N hydrochloric acid, 120 ml of water, 120 ml of a saturated aqueous sodium hydrogen carbonate solution and 120 ml of water. After drying over magnesium sulphate and evaporation, the residue is taken up in cyclohexane and triturated, and a solid is removed by filtration; the filtrate is concentrated (13.3 g ) and then chromatographed on 1 kg of silica (eluant: dichloromethane) to yield 11.2 g of the desired product (yield: 82%).

Provenance & Evidence