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

HRID 923244Notes

Reaction equation

HRID 923244 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.N1C=CN=C1.[Si:33](Cl)([C:36]([CH3:39])([CH3:38])[CH3:37])([CH3:35])[CH3:34]>C(Cl)Cl>[Si: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)([C:36]([CH3:39])([CH3:38])[CH3:37])([CH3:35])[CH3:34]

Participants

5

Reactant 3

HCID 795ImidazoleHCID 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 1

HCID 6344DichloromethaneSolvent

Procedure

2-(1-Trityl-1H-imidazol-4-yl)ethanol (20 g, 56.5 mmol) is dissolved in CH2Cl2 (500 mL). To this is added imidazole (11.5 g, 169 mmol) and tert-butyldimethylsilylchloride (10.2 g, 67.8 mmol). The solution is stirred at room temperature until LCMS indicated the reaction is complete. The solution is partitioned between CH2Cl2 and aqueous saturated NaHCO3. The organic layer is washed further with aqueous saturated NaHCO3 and brine.

Workup

  1. customThe solution is partitioned between CH2Cl2 and aqueous saturated NaHCO3
  2. washThe organic layer is washed further with aqueous saturated NaHCO3 and brine

Sources & evidence

ORD record
ord-3937c13eb5864d1cac28b286c94c1b35
Source dataset
uspto-grants-2016_03
Patent number
US09278969B2

Reaction notes

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