Oxetane → 2-Oxaspiro[5.5]undecan-1-ol

Participants

Reaction Steps

To a mixture of 44 g of ethylmagnesium bromide and 120 g of tetrahydrofuran was added a mixture of 50 g of cyclohexylmethylenecyclohexylamine and 50 g of tetrahydrofuran. The resulting mixture was stirred for 2 hours under tetrahydrofuran reflux conditions. Thereafter, 21 g of oxetane was added under ice cooling to the reaction mixture, which was stirred for a further 20 hours at room temperature. Then 30 g of acetic acid was added to quench the reaction, followed by ordinary aqueous workup, obtaining 67 g of a crude product, 1-[(1-cyclohexyliminomethyl)cyclo-hexyl]propan-1-ol. To 67 g of the crude product were added 16 g of acetic acid, 400 g of hexane, and 280 g of water. The mixture was stirred at 50° C. for 12 hours. The reaction mixture was then subjected to ordinary aqueous workup and distillation for purification, obtaining 22 g (yield 500) of the target compound, 2-oxaspiro[5.5]undecan-1-ol.

Provenance & Evidence