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

HRID 1722765

반응식

HRID 1722765 반응식
[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]=1

참가 물질

5

반응물 3

HCID 844611-(Trimethylsilyl)pyrrolidin-2-oneHCID 103209955-[5-(2,6-Dichloro-4-iodophenoxy)pentyl]-3-methylisoxazoleHCID 178418339Butyllithium

생성물 1

HCID 5154365-{5-[2,6-dichloro-4-(4,5-dihydro-3H-pyrrol-2-yl)phenoxy]pentyl}-3-methylisoxazole수율 41.6%

시약·촉매·용매 1

HCID 3283Diethyl Ether용매2회

실험 절차

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.

후처리

  1. customto come to room temperature
  2. washwas washed with water
  3. dry with materialdried over potassium carbonate
  4. customThe product was isolated
  5. customchromatographed (3:1 hexane:ethyl acetate)
  6. customrecrystallized from isopropyl acetate/hexane

출처 및 근거

ORD 기록
ord-26cc03085bae439981e78440a35c9abb
출처 데이터셋
uspto-grants-1989_08
특허 번호
US04857539

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