1-(Trimethylsilyl)pyrrolidin-2-one → 5-{5-[2,6-dichloro-4-(4,5-dihydro-3H-pyrrol-2-yl)phenoxy]pentyl}-3-methylisoxazole
Reaction equation
[Cl:1][C:2]1[CH:19]=[C:18](I)[CH:17]=[C:16]([Cl:21])[C:3]=1[O:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][C:10]1[O:14][N:13]=[C:12]([CH3:15])[CH:11]=1.C([Li])CCC.C[Si](C)(C)[N:29]1[CH2:33][CH2:32][CH2:31][C:30]1=O>CCOCC>[Cl:1][C:2]1[CH:19]=[C:18]([C:30]2[CH2:31][CH2:32][CH2:33][N:29]=2)[CH:17]=[C:16]([Cl:21])[C:3]=1[O:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][C:10]1[O:14][N:13]=[C:12]([CH3:15])[CH:11]=1Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
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.
Workup
- customto come to room temperature
- washwas washed with water
- dry with materialdried over potassium carbonate
- customThe product was isolated
- customchromatographed (3:1 hexane:ethyl acetate)
- customrecrystallized from isopropyl acetate/hexane
Sources & evidence
- ORD record
- ord-26cc03085bae439981e78440a35c9abb
- Source dataset
- uspto-grants-1989_08
- Patent number
- US04857539
Reaction notes
Loading…