Water → 1-(4-bromo-2-fluorobenzyl)-2-(n-propyl)-4-ethyl-5-(2-(phenoxy)phenoxy)acetyl-1H-imidazole

HRID 1078050

반응식

HRID 1078050 반응식
[O:1]([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1[OH:14])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C([O-])([O-])=O.[K+].[K+].[Br:21][C:22]1[CH:42]=[CH:41][C:25]([CH2:26][N:27]2[C:31]([C:32](=[O:35])[CH2:33]Br)=[C:30]([CH2:36][CH3:37])[N:29]=[C:28]2[CH2:38][CH2:39][CH3:40])=[C:24]([F:43])[CH:23]=1.O>CC(C)=O>[Br:21][C:22]1[CH:42]=[CH:41][C:25]([CH2:26][N:27]2[C:31]([C:32](=[O:35])[CH2:33][O:14][C:9]3[CH:10]=[CH:11][CH:12]=[CH:13][C:8]=3[O:1][C:2]3[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=3)=[C:30]([CH2:36][CH3:37])[N:29]=[C:28]2[CH2:38][CH2:39][CH3:40])=[C:24]([F:43])[CH:23]=1

참가 물질

6

반응물 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 754912-Hydroxydiphenyl etherHCID 194304911-(4-bromo-2-fluorobenzyl)-2-(n-propyl)-4-ethyl-5-bromoacetyl-1H-imidazole

생성물 1

HCID 194304711-(4-bromo-2-fluorobenzyl)-2-(n-propyl)-4-ethyl-5-(2-(phenoxy)phenoxy)acetyl-1H-imidazole수율 13%

시약·촉매·용매 1

HCID 180Acetone용매2회

실험 절차

To a solution of 0.63 g (3.36 mmol) of 2-phenoxyphenol and 0.62 g (4.48 mmol) of K2CO3 in 75 mL acetone at ambient temperature was added 1.00 g (2.24 mmol) of 1-(4-bromo-2-fluorobenzyl)-2-(n-propyl)-4-ethyl-5-bromoacetyl-1H-imidazole obtained from Part B of Example 11 in 25 mL acetone. After stirring at reflux overnight, the reaction mixture was poured into water and extracted with 3×100 mL ethyl acetate. The combined organic layers were washed with brine, dried over MgSO4, filtered, and the solvents evaporated under reduced pressure. The crude product was purified by flash column chromatography using 10-40% ethyl acetate in hexane, which provided 0.16 g (6.3%) of a clear oil after evaporation of solvents under reduced pressure. 1H NMR (300 MHz, CDCl3): δ 0.95 (t, 3H, J=7.3 Hz); 1.29 (t, 3H, J =7.3 Hz); 1.66 (m, 2H); 2.60 (m, 2H); 2.81 (q, 2H, J=7.3 Hz); 5.00 (s, 2H); 6.38 (t, 1H, J=7.8 Hz); 6.89-7.29 (m, 10H). ##STR106##

후처리

  1. temperatureat reflux overnight
  2. extractionextracted with 3×100 mL ethyl acetate
  3. washThe combined organic layers were washed with brine
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. customthe solvents evaporated under reduced pressure
  7. customThe crude product was purified by flash column chromatography

출처 및 근거

ORD 기록
ord-b418881cfedc4d088b2244dcd50d3642
출처 데이터셋
uspto-grants-1996_08
특허 번호
US05545651

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