Imidazole → (2-Azidoethoxy)(tert-butyl)dimethylsilane

HRID 1650327Notes

Reaction equation

HRID 1650327 reaction equation
[N:1]([CH2:4][CH2:5][OH:6])=[N+:2]=[N-:3].[C:7]([Si:11](Cl)([CH3:13])[CH3:12])([CH3:10])([CH3:9])[CH3:8].N1C=CN=C1.O>CN(C)C=O>[N:1]([CH2:4][CH2:5][O:6][Si:11]([C:7]([CH3:10])([CH3:9])[CH3:8])([CH3:13])[CH3:12])=[N+:2]=[N-:3]

Participants

6

Reactant 4

HCID 795ImidazoleHCID 962WaterHCID 28928tert-Butyldimethylsilyl chlorideHCID 1231182-Azidoethanol

Product 1

HCID 14024254(2-Azidoethoxy)(tert-butyl)dimethylsilaneYield 94.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

2. 2-Azidoethanol, 1, (105 g, 1.21 mol), crude from above preparation, and tert-butylchlorodimethylsilane (200 g. 1.33 mol) were dissolved in 200 mL of dry N,N-dimethylformamide (DMF) and stirred under nitrogen. Over a period of 20 min, imidazole (204 g, 3.00 mol) was added portionwise with stirring and the temperature of the reaction rose to about 40° C. The solution was stirred at 40° C. under nitrogen for 24 h. The reaction mixture was cooled to room temperature, poured into 1 L of water, and extracted with pentane (4×300 mL). The pentane layers were dried over anhydrous sodium sulfate, concentrated on a rotary evaporator at 25° C., and distilled at reduced pressure through a 4 in. Vigreux column to give 230 g (1.14 mol, 94.7%) of 1-azido-2-(tert-butyldimethylsiloxy)ethane, 2: bp 37°-39° C. (0.02 mm); IR (CH2Cl2) 2940, 2860, 2120, 1115, 940, 840 cm10-1,1H NMR (CDl3, Me4Si) δ 0.09 6H,s), 0.92 (9H,s), 3.27 (2H,t,J=5 Hz), 3.80 (2H,t,J=5 Hz); proton decoupled 13C NMR (CDCl3, Me4Si)) δ-5.54, 18.18, 25.77, 53.16, 62.59.

Workup

  1. stirringwith stirring
  2. customrose to about 40° C
  3. stirringThe solution was stirred at 40° C. under nitrogen for 24 h
  4. extractionextracted with pentane (4×300 mL)
  5. dry with materialThe pentane layers were dried over anhydrous sodium sulfate
  6. concentrationconcentrated on a rotary evaporator at 25° C.
  7. distillationdistilled at reduced pressure through a 4 in

Sources & evidence

ORD record
ord-7ce0f1f8d075483c92d4980a9cdf91b3
Source dataset
uspto-grants-1990_05
Patent number
US04923970

Reaction notes

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