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

HRID 2273303

Reaction equation

HRID 2273303 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.C(N(CC)CC)C.[Si:23](Cl)([C:36]([CH3:39])([CH3:38])[CH3:37])([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>ClCCl.CN(C1C=CN=CC=1)C>[Si:23]([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:36]([CH3:39])([CH3:38])[CH3:37])([C:30]1[CH:31]=[CH:32][CH:33]=[CH:34][CH:35]=1)[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1

Participants

6

Reactant 3

HCID 8471Triethylamine2×HCID 94078tert-Butyldiphenylchlorosilane2×HCID 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)pyridineCatalyst2×HCID 6344DichloromethaneSolvent

Procedure

1-(2-Trimethylsilylethoxymethyl)-1H-imidazole-4-methanol (100 g, WO 01/02145) was dissolved in dichloromethane (1 L), and triethylamine (hereinafter sometimes referred to as TEA) (122 mL), 4-(N,N-dimethylamino)pyridine (hereinafter sometimes referred to as DMAP) (5.35 g) and tert-butyldiphenylsilyl chloride (hereinafter sometimes referred to as TBDPSCl) (149 mL) were added under stirring. After stirring for a day, the reaction mixture was washed with water and dried over anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure. The resulting residue was purified by flash chromatography (ethyl acetate/hexane=25%→50%) using a silica gel column (trade name: Ultrapack E, manufactured by Yamazen Corporation) to give the title compound (146 g).

Workup

  1. additionwere added
  2. stirringAfter stirring for a day
  3. washthe reaction mixture was washed with water
  4. dry with materialdried over anhydrous sodium sulfate
  5. distillationthe solvent was distilled off under reduced pressure
  6. customThe resulting residue was purified by flash chromatography (ethyl acetate/hexane=25%→50%)

Sources & evidence

ORD record
ord-cc135a832b9343f7a4ab23eb361777f7
Source dataset
uspto-grants-2015_09
Patent number
US09120835B2

Linked notes

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