tert-Butyldiphenylchlorosilane → 4-(tert-Butyldiphenylsilyloxymethyl)-1-(2-trimethylsilylethoxy methyl)-1H-imidazole

HRID 242386

Reaction equation

HRID 242386 reaction equation
[CH3:1][Si:2]([CH3:15])([CH3:14])[CH2:3][CH2:4][O:5][CH2:6][N:7]1[CH:11]=[C:10]([CH2:12][OH:13])[N:9]=[CH:8]1.[CH3:16][C:17]([Si:20](Cl)([C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)([CH3:19])[CH3:18]>ClCCl.CN(C1C=CN=CC=1)C>[Si:20]([O:13][CH2:12][C:10]1[N:9]=[CH:8][N:7]([CH2:6][O:5][CH2:4][CH2:3][Si:2]([CH3:15])([CH3:14])[CH3:1])[CH:11]=1)([C:17]([CH3:19])([CH3:18])[CH3:16])([C:27]1[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=1)[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1

Participants

5

Reactant 2

HCID 94078tert-ButyldiphenylchlorosilaneHCID 695583761-(2-Trimethylsilylethoxymethyl)-1H-imidazole-4-methanol

Product 1

HCID 710872934-(tert-Butyldiphenylsilyloxymethyl)-1-(2-trimethylsilylethoxy methyl)-1H-imidazole

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

1-(2-Trimethylsilylethoxymethyl)-1H-imidazole-4-methanol (100 g) was dissolved in dichloromethane (1 L), and under stirring TEA (122 mL), DMAP (5.35 g), and then TBDPSCl (149 mL) were added. After stirring for 1 day, the reaction mixture solution was washed with water, dried over anhydrous sodium sulfate, and subsequently the solvent was distilled off under reduced pressure. The resulting residue was purified by flash chromatography (ethyl acetate/hexane=25%-50%) using silica gel column (product name: Ultra Pack E, manufactured by Yamazen Corporation) to afford the title compound (146 g).

Workup

  1. washthe reaction mixture solution was washed with water
  2. dry with materialdried over anhydrous sodium sulfate
  3. distillationsubsequently the solvent was distilled off under reduced pressure
  4. customThe resulting residue was purified by flash chromatography (ethyl acetate/hexane=25%-50%)

Sources & evidence

ORD record
ord-0740e4e2a6d74c7680fc97aab1e42bee
Source dataset
uspto-grants-2014_02
Patent number
US08653126B2

Linked notes

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