Imidazole → 4-(2-((tert-Butyldimethylsilyl)oxy)ethyl)-1-trityl-1H-imidazole

HRID 1690747Notes

Reaction equation

HRID 1690747 reaction equation
[C:1]([N:20]1[CH:24]=[C:23]([CH2:25][CH2:26][OH:27])[N:22]=[CH:21]1)([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:28]([Si:32](Cl)([CH3:34])[CH3:33])([CH3:31])([CH3:30])[CH3:29].CN(C1C=CC=CN=1)C.N1C=CN=C1>CN(C=O)C.C(OCC)(=O)C>[C:28]([Si:32]([CH3:34])([CH3:33])[O:27][CH2:26][CH2:25][C:23]1[N:22]=[CH:21][N:20]([C:1]([C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=2)([C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=2)[C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)[CH:24]=1)([CH3:31])([CH3:30])[CH3:29]

Participants

7

Reactant 4

HCID 795ImidazoleHCID 218852-DimethylaminopyridineHCID 28928tert-Butyldimethylsilyl chlorideHCID 106894902-(1-Trityl-1H-imidazol-4-yl)ethanol

Product 1

HCID 668853594-(2-((tert-Butyldimethylsilyl)oxy)ethyl)-1-trityl-1H-imidazole

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 2-(1-trityl-1H-imidazol-4-yl)-ethanol (5.21 g, 14.7 mmol) in DMF (20 mL) is added tert-butylchlorodimethylsilane (2.44 g, 16.1 mmol), dimethylaminopyridine (0.179 g, 1.47 mmol) and imidazole (3.00 g, 44.1 mmol). The reaction mixture is stirred for 2 h at room temperature. It is then diluted with ethyl acetate and washed with water thrice. The organic phase is dried over Na2SO4 and concentrated in vacuo. The residue is purified by silica gel chromatography (hexane-ethanol, 7:3) to give 4-[2-(tert-butyl-dimethyl-silanyloxy)-ethyl]-1-trityl-1H-imidazole product, which is used in the next step without further purification; MS (ESI) m/z 469.3 (M+H)

Workup

  1. washwashed with water thrice
  2. dry with materialThe organic phase is dried over Na2SO4
  3. concentrationconcentrated in vacuo
  4. customThe residue is purified by silica gel chromatography (hexane-ethanol, 7:3)

Sources & evidence

ORD record
ord-b593a095d3ee453394363d2a9325af9e
Source dataset
uspto-grants-2012_04
Patent number
US08153674B2

Reaction notes

Loading…