反应详情

To a stirred solution of 1,4-dioxaspiro[4.5]decan-8-ol (Intermediate M) (99.8 g, 0.63 mol) in pyridine (450 mLs) at 0° C. under nitrogen was added tosylchloride (132.4 g, 0.69 mol) portionwise such that T<2° C. On complete addition, the mixture was allowed to warm slowly to room temperature and stirred at room temperature overnight. Treated with water (750 mL) and extracted with EtOAc (500 mL then 2×250 mL). Combined extracts were washed with 3N HCl (3×300 mL), brine (300 mL) and dried over Na2SO4. Filtered and evaporated to yield a pale yellow oil (200 g crude). This oil was treated with petroleum ether (40-60°) (200 mL) and scratched to induce solid formation. 1,4-dioxaspiro[4.5]dec-8-yl 4-methyl-1-benzenesulfonate was filtered, washed with petroleum ether (40-60°) (200 mL) and dried in vacuo. Yield=181.0 g, 92%.

1. additionOn complete addition
2. extractionextracted with EtOAc (500 mL
3. washCombined extracts were washed with 3N HCl (3×300 mL), brine (300 mL)
4. dry with materialdried over Na2SO4
5. filtrationFiltered
6. customevaporated
7. customto yield a pale yellow oil (200 g crude)
8. filtration1,4-dioxaspiro[4.5]dec-8-yl 4-methyl-1-benzenesulfonate was filtered
9. washwashed with petroleum ether (40-60°) (200 mL)
10. customdried in vacuo