(3,5-Di-tert-butyl-4-hydroxy-phenyl)-(3-hydroxy-azetidin-1-yl)-methanone → 1-(3,5-Di-tert-butyl-4-hydroxy-benzyl)-azetidin-3-ol

Participants

Reaction Conditions

Reaction Steps

A suspension of lithium aluminium hydride (1,35 g, 36,7 mmoles) in anhydrous tetrahydrofuran (60 ml) was cooled to 0° C., and a solution of (3,5-di-tert-butyl-4-hydroxy-phenyl)-(3-hydroxy-azetidin-1-yl)-methanone (1,78 g, 6,12 mmoles) in anhydrous tetrahydrofuran (40 ml) was added. The cooling bath was removed, the mixture was stirred at room temperature overnight and then heated to reflux for 5 hours. The mixture was then cooled to 0° C. and the excess of the reducing agent was eliminated by the addition of a saturated solution of ammonium chloride. The mixture is filtered and the filtrate was evaporated to dryness by use of a rotavapor. The residue was dissolved in diethyl ether, the resulting solution washed with water, dried over sodium sulfate and evaporated to dryness with a rotavapor. The resulting crude solid was crystallized from chloroform/petrol ether to give 1,33 g (75% of theoretical yield) of the desired product having a melting point of 139–142° C.

Provenance & Evidence