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

HRID 1985217Notes

Reaction equation

HRID 1985217 reaction equation
[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]

Participants

5

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-7a35504686194b67bcf93300d94e794e
Source dataset
uspto-grants-2009_06
Patent number
US07544812B2

Reaction notes

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