1-(Trimethylsilyl)pyrrolidin-2-one → 5-{5-[2,6-dichloro-4-(4,5-dihydro-3H-pyrrol-2-yl)phenoxy]pentyl}-3-methylisoxazole

Beteiligte Stoffe

Reaktionsschritte

To a solution of 5.0 g 5-[5-(2,6-dichloro-4-iodophenoxy)pentyl]-3-methylisoxazole (Example 12a) in 75 ml dry ether cooled to -78° C. under nitrogen was added 1.4 ml n-butyllithium (9.5 m). A solution of 1.8 g 1-trimethylsilylpyrrolidin-2-one [cf. Feringa et al., Tetrahedron Letters, 507 (1986)] in ether was then added dropwise. The reaction mixture was allowed slowly to come to room temperature, and was washed with water and dried over potassium carbonate. The product was isolated and chromatographed (3:1 hexane:ethyl acetate) and recrystallized from isopropyl acetate/hexane to give 1.8 g 5-{5-[2,6-dichloro-4-(4,5-dihydro-3H-pyrrol-2-yl)phenoxy]pentyl}-3-methylisoxazole, m.p. 57-59° C.

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