反应详情

温度

80 °C

To a solution of (tetrahydro-3-furanyl)methyl 4-methylbenzenesulfonate (i.e., the product of Step A) (11.0 g, 42.9 mmol) in N,N-dimethylformamide (160 mL) was added potassium phthalimide (7.9 g, 42.7 mmol) in one portion, and the resulting mixture was stirred at 80° C. for 6 h. Additional potassium phthalimide (5 g, 27 mmol) was added, and stirring was continued at 100° C. for 18 h. The cooled reaction mixture was partitioned between water and ethyl acetate and the aqueous layer was separated and extracted with ethyl acetate (5×75 mL). The combined extracts were dried over MgSO4 and filtered, and the solvent was removed under reduced pressure to give a residue which was chromatographed on silica gel (40 g) eluted with 5% to 100% ethyl acetate in hexanes to give 4.5 g of the title compound as a white solid, m.p. 114-118° C.

1. stirringstirring
2. waitwas continued at 100° C. for 18 h
3. customThe cooled reaction mixture
4. customwas partitioned between water and ethyl acetate
5. customthe aqueous layer was separated
6. extractionextracted with ethyl acetate (5×75 mL)
7. dry with materialThe combined extracts were dried over MgSO4
8. filtrationfiltered
9. customthe solvent was removed under reduced pressure
10. customto give a residue which
11. customwas chromatographed on silica gel (40 g)
12. washeluted with 5% to 100% ethyl acetate in hexanes