4-Toluenesulfonyl chloride → 1,4-Dioxaspiro[4.5]decan-8-ol, 8-(4-methylbenzenesulfonate)

Participants

Reaction Steps

A solution of 1,4-dioxa-spiro[4.5]decan-8-ol (prepared according to the procedure of Kayser, Margaret M.; Clouthier, Christopher M. Journal of Organic Chemistry (2006), 71(22), 8424-8430, 11 g, 70 mmol) in DCM (100 mL) was treated with TEA (11 mL, 77 mmol) followed by TsCl (Aldrich, 13.3 g, 70 mmol) slowly at 0° C. The reaction was warmed to room temperature over 2 hours. The solution was partitioned between DCM and water. The organic layer was washed with brine, dried over anhydrous Na2SO4, filtered and concentrated to give white solid, which was then purified by silica gel column on a CombiFlash® system (Teledyne Isco, Inc, Lincoln, Neb.) system using hexanes and ethyl acetate (from 10% ethyl acetate to 100% ethyl acetate) to afford the title compound as white solid.

Provenance & Evidence