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

HRID 1985217ノート

反応式

HRID 1985217 の反応式
[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]

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-7a35504686194b67bcf93300d94e794e
出典データセット
uspto-grants-2009_06
特許番号
US07544812B2

反応ノート

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