反应详情

A stirred mixture of 4.02 g (0.01 mole) of crude (73%) 2-methyl-3-[3-(trifluoromethyl)phenoxy]-1-azetidinecarbonyl chloride cis isomer and 1.4 g (0.01 mole) of potassium carbonate in 20 ml of tetrahydrofuran was treated with 0.57 g (0.01 mole) of 2-propenylamine. After stirring for 15 minutes, a small piece of ice was added and stirring continued for 3 hr. The reaction mixture was diluted with water and the oil which separated was extracted with methylene chloride (2×50 ml). The combined extracts were dried over magnesium sulfate and concentrated in vacuo (5.2 g). The crude product was chromatographed on a 125 g silica gel column. Elution with chloroform washed impurities from the column and the product was removed by eluting with an ethyl acetate/chloroform gradient (1-20%). The combined product fractions gave a pale yellow oil which solodified on standing and was recrystallized from isopropyl ether/hexane to give an oil which slowly crystallized, yielding 2.1 g (67.8%) of white product, m.p. 74°-77° C.

1. additiona small piece of ice was added
2. stirringstirring
3. waitcontinued for 3 hr
4. customthe oil which separated
5. extractionwas extracted with methylene chloride (2×50 ml)
6. dry with materialThe combined extracts were dried over magnesium sulfate
7. concentrationconcentrated in vacuo (5.2 g)
8. customThe crude product was chromatographed on a 125 g silica gel column
9. washElution with chloroform washed impurities from the column
10. customthe product was removed
11. washby eluting with an ethyl acetate/chloroform gradient (1-20%)
12. customThe combined product fractions gave a pale yellow oil which
13. customwas recrystallized from isopropyl ether/hexane
14. customto give an oil which
15. customslowly crystallized