反应详情

To a solution of tetrahydro-pyran-4-carbaldehyde oxime (6.5 g, 50 mmol) in DMF (47 mL) was added N-chlorosuccinimide (6.95 g, 50 mmol) at room temperature and the after 3 h the mixture was extracted with tert-butylmethylether (100 mL). The organic extract was then added dropwise over 2 h to a solution of ethyl 2-butynoate (61.2 mL, 52.5 mmol) and triethylamine (8.4 mL, 60 mmol) in tert-butylmethylether (47 mL) heated under reflux and the resulting mixture heated overnight. The reaction mixture was then cooled to room temperature and extracted with tert-butylmethylether and washed with aqueous hydrochloric acid solution (1 N). The combined organic phases were dried over sodium sulfate, filtered and concentrated. Purification by chromatography (silica, heptane:ethyl acetate=100:0 to 1:1) afforded the title compound (4.2 g, 35%) as a light yellow solid. MS: m/e=240.2 [M+H]+.

1. extractionthe after 3 h the mixture was extracted with tert-butylmethylether (100 mL)
2. extractionThe organic extract
3. temperatureheated
4. temperatureunder reflux
5. temperaturethe resulting mixture heated overnight
6. extractionextracted with tert-butylmethylether
7. washwashed with aqueous hydrochloric acid solution (1 N)
8. dry with materialThe combined organic phases were dried over sodium sulfate
9. filtrationfiltered
10. concentrationconcentrated
11. customPurification by chromatography (silica, heptane:ethyl acetate=100:0 to 1:1)