[O:1]1[CH2:6][CH2:5][C:4](=[O:7])[CH2:3][CH2:2]1.Cl[CH2:9][C:10]#[N:11].CC(C)([O-])C.[K+]>C(O)(C)(C)C.O>[O:7]1[C:4]2([CH2:5][CH2:6][O:1][CH2:2][CH2:3]2)[CH:9]1[C:10]#[N:11]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%).
Wird geladen…
