Sodium hydride → 5-[2-(Tert-butyl-diphenyl-silanyloxy)-ethyl]-3-(4-methyl-benzyl)-1-propyl-imidazolidine-2,4-dione

HRID 1985217

반응식

HRID 1985217 반응식
[C:1]([Si:5]([C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1)([C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)[O:6][CH2:7][CH2:8][CH:9]1[NH:13][C:12](=[O:14])[N:11]([CH2:15][C:16]2[CH:21]=[CH:20][C:19]([CH3:22])=[CH:18][CH:17]=2)[C:10]1=[O:23])([CH3:4])([CH3:3])[CH3:2].[H-].[Na+].[CH2:38](I)[CH2:39][CH3:40]>CN(C=O)C>[C:1]([Si:5]([C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1)([C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)[O:6][CH2:7][CH2:8][CH:9]1[N:13]([CH2:38][CH2:39][CH3:40])[C:12](=[O:14])[N:11]([CH2:15][C:16]2[CH:21]=[CH:20][C:19]([CH3:22])=[CH:18][CH:17]=2)[C:10]1=[O:23])([CH3:4])([CH3:2])[CH3:3]

참가 물질

5

반응물 3

HCID 24758Sodium hydrideHCID 336431-IodopropaneHCID 577192895-[2-(Tert-butyl-diphenyl-silanyloxy)-ethyl]-3-(4-methyl-benzyl)-imidazolidine-2,4-dione

생성물 1

HCID 577192585-[2-(Tert-butyl-diphenyl-silanyloxy)-ethyl]-3-(4-methyl-benzyl)-1-propyl-imidazolidine-2,4-dione수율 96%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

A 0° C. solution of 5-[2-(tert-butyl-diphenyl-silanyloxy)-ethyl]-3-(4-methyl-benzyl)-imidazolidine-2,4-dione (14.26 g, 29.3 mmol) in DMF (250 mL) was treated with sodium hydride (60% dispersion, 1.29 g, 32.2 mmol) and warmed to room temperature and stirred under N2 for 30 minutes. The resultant mixture was cooled to 0° C. and then treated with 1-propyl iodide (5.47 g, 32.2 mmol) and then warmed to room temperature and stirred for 3 h. The reaction was quenched with aqueous 1 N HCl (60 mL) and then worked up extractively with diethyl ether and water. The organic layer was dried (MgSO4) and the solvent removed in vacuo to give crude product that was purified by flash chromatography using 6:1 hexanes:acetone to afford 14.8 g (96%) 5-[2-(tert-butyl-diphenyl-silanyloxy)-ethyl]-3-(4-methyl-benzyl)-1-propyl-imidazolidine-2,4-dione. MS (ES+) Calc'd for C32H40N2O3Si (M+1) 529. Found m/z 529 (100%). 1H NMR.

후처리

  1. temperaturewarmed to room temperature
  2. stirringstirred for 3 h
  3. customThe reaction was quenched with aqueous 1 N HCl (60 mL)
  4. dry with materialThe organic layer was dried (MgSO4)
  5. customthe solvent removed in vacuo
  6. customto give crude product that
  7. customwas purified by flash chromatography

출처 및 근거

ORD 기록
ord-7a35504686194b67bcf93300d94e794e
출처 데이터셋
uspto-grants-2009_06
특허 번호
US07544812B2

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