Imidazole → HCID 21936008, compound

HRID 1371490Notes

Reaction equation

HRID 1371490 reaction equation
[Si:1](Cl)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].[OH:9][CH2:10][CH2:11][N:12]1[C:16]([CH3:17])=[CH:15][N:14]=[CH:13]1.N1C=CN=C1.C(Cl)Cl>O>[Si:1]([O:9][CH2:10][CH2:11][N:12]1[C:16]([CH3:17])=[CH:15][N:14]=[CH:13]1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2]

Participants

6

Reactant 4

HCID 795ImidazoleHCID 6344DichloromethaneHCID 28928tert-Butyldimethylsilyl chlorideHCID 11557283HCID 11557283, compound

Product 1

HCID 21936008HCID 21936008, compoundYield 95.9%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
0 °C

Procedure

Tert-butyldimethylsilyl chloride (9.05 g) was added to a stirred mixture of 1-(2-hydroxyethyl)-5-methylimidazole (6.4 g), imidazole (7.5 g) and methylene chloride (30 ml) which was cooled to 0° C. The reaction mixture was stirred at ambient temperature for 4 hours. The mixture was poured into water. The organic layer was washed with brine, dried over magnesium sulphate and evaporated to give 1-(2-tert-butyldimethylsilyloxyethyl)-5-methylimidazole (11.7 g); NMR Spectrum: (CDCl3) −0.04 (s, 6H), 0.85 (s, 6H), 2.2 (s, 3H), 3.8 (m, 2H), 3.94 (m, 2H), 6.75 (s, 1H), 7.43 (s, 1H).

Workup

  1. washThe organic layer was washed with brine
  2. dry with materialdried over magnesium sulphate
  3. customevaporated

Sources & evidence

ORD record
ord-5d9952aa5e5847cc9744d3ec2644b0e7
Source dataset
uspto-grants-2007_01
Patent number
US07157467B2

Reaction notes

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