Imidazole → 4-(2-{[tert-Butyl(dimethyl)silyl]oxy}propoxy)benzaldehyde

HRID 2362822Notes

Reaction equation

HRID 2362822 reaction equation
[Si:1](Cl)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].N1C=CN=C1.[OH:14][CH:15]([CH3:26])[CH2:16][O:17][C:18]1[CH:25]=[CH:24][C:21]([CH:22]=[O:23])=[CH:20][CH:19]=1.C(=O)(O)[O-].[Na+]>CN(C)C=O>[Si:1]([O:14][CH:15]([CH3:26])[CH2:16][O:17][C:18]1[CH:25]=[CH:24][C:21]([CH:22]=[O:23])=[CH:20][CH:19]=1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2]

Participants

6

Reactant 4

HCID 795ImidazoleHCID 28928tert-Butyldimethylsilyl chlorideHCID 516892Sodium BicarbonateHCID 574320794-(2-Hydroxypropoxy)benzaldehyde

Product 1

HCID 592019704-(2-{[tert-Butyl(dimethyl)silyl]oxy}propoxy)benzaldehyde

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

5.39 g (35.7 mmol) of tert-butyldimethylsilyl chloride and 3.30 g (48.5 mmol) of imidazole are added successively to a solution of 4.60 g (25.5 mmol) of the compound from Example 40A in 120 ml of dry dimethylformamide, and the mixture is stirred at RT for 20 h. 100 ml of saturated sodium bicarbonate solution are then added, and the reaction mixture is extracted with diethyl ether (three times, 100 ml each). The combined organic phases are dried over magnesium sulphate. After removal of the solvent on a rotary evaporator, the crude product is purified chromatographically on silica gel 60 (mobile phase gradient cyclohexane/ethyl acetate 50:1→10:1).

Workup

  1. extractionthe reaction mixture is extracted with diethyl ether (three times, 100 ml each)
  2. dry with materialThe combined organic phases are dried over magnesium sulphate
  3. customAfter removal of the solvent
  4. customon a rotary evaporator
  5. customthe crude product is purified chromatographically on silica gel 60 (mobile phase gradient cyclohexane/ethyl acetate 50:1→10:1)

Sources & evidence

ORD record
ord-84321affe6be40f3a8a0e9fa0858ede9
Source dataset
uspto-grants-2014_04
Patent number
US08691850B2

Reaction notes

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