反应详情

Dissolve tetrahydropyran-4-one (5.0 mL, 54.2 mmol) and chloroacetonitrile (3.4 mL, 53.5 mmol) in tert-butanol (1 mL) and add drop-wise a solution of potassium tert-butoxide (54 mL, 54 mmol, 1.0 M in tert-butanol) over 20 minutes. Stir for 16 hours, dilute with water and quench slowly with 1 N hydrochloric acid. Extract with diethyl ether (×3). Combine extracts and wash with saturated aqueous sodium chloride solution, dry (magnesium sulfate), filter, concentrate and purify (silica gel chromatography, eluting with 0:100 to 1:1 ethyl acetate:hexanes) to give the desired compound as a light yellow oil (4.4 g, 59%).

1. additionadd
2. customover 20 minutes
3. customquench slowly with 1 N hydrochloric acid
4. extractionExtract with diethyl ether (×3)
5. washCombine extracts and wash with saturated aqueous sodium chloride solution
6. dry with materialdry (magnesium sulfate)
7. filtrationfilter
8. concentrationconcentrate
9. custompurify
10. wash(silica gel chromatography, eluting with 0:100 to 1:1 ethyl acetate:hexanes)