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

HRID 532904Notes

Reaction equation

HRID 532904 reaction equation
[NH:1]1[CH:5]=[C:4]([CH2:6][CH2:7][OH:8])[N:3]=[CH:2]1.N1C=CN=C1.[CH3:14][C:15]([Si:18](Cl)([C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)([CH3:17])[CH3:16]>CN(C=O)C>[Si:18]([O:8][CH2:7][CH2:6][C:4]1[N:3]=[CH:2][NH:1][CH:5]=1)([C:15]([CH3:17])([CH3:16])[CH3:14])([C:25]1[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=1)[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1

Participants

5

Reactant 3

HCID 795ImidazoleHCID 94078tert-ButyldiphenylchlorosilaneHCID 178520346HCID 178520346, compound

Product 1

HCID 1784555164-(2-((tert-butyldiphenylsilyl)oxy)ethyl)-1H-imidazoleYield 41.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 2-(1H-imidazol-4-yl)ethanol (1.24 g, 11.1 mmol) in DMF (10 mL) was treated with imidazole (1.51 g, 22.1 mmol) and TBDPSCl (3.12 mL, 12.2 mmol) and the mixture was stirred at RT for 2 h. The mixture was then poured onto H2O and extracted with AcOEt. The combined org. layers were dried over Na2SO4, filtered and concentrated in vacuo. Purification by flash chromatography (SiO2, AcOEt/heptane 0:100 to 100:0) gave the title compound (1.6 g). UPLC-MS: MS 351.2 (M+H+); UPLC rt 1.02 min.

Workup

  1. additionThe mixture was then poured onto H2O
  2. extractionextracted with AcOEt
  3. dry with materiallayers were dried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customPurification by flash chromatography (SiO2, AcOEt/heptane 0:100 to 100:0)

Sources & evidence

ORD record
ord-07bf9999e4c94f7685b490350203a9a4
Source dataset
uspto-grants-2014_10
Patent number
US08853203B2

Reaction notes

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