Water → 2-(3{[tert-Butyl(dimethyl)silyl]oxy}propyl)-1H-benzimidazole

HRID 1610796

Reaction equation

HRID 1610796 reaction equation
[Si:1](Cl)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].[OH:9][CH2:10][CH2:11][CH2:12][C:13]1[NH:14][C:15]2[CH:21]=[CH:20][CH:19]=[CH:18][C:16]=2[N:17]=1.C(N(CC)CC)C.O>CN(C=O)C>[Si:1]([O:9][CH2:10][CH2:11][CH2:12][C:13]1[NH:14][C:15]2[CH:21]=[CH:20][CH:19]=[CH:18][C:16]=2[N:17]=1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2]

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 28928tert-Butyldimethylsilyl chlorideHCID 754702-Benzimidazolepropanol

Product 1

HCID 695919622-(3{[tert-Butyl(dimethyl)silyl]oxy}propyl)-1H-benzimidazoleYield 97.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To this end, tert-butyldimethylsilyl chloride (TBDMSCI) (14.68 g, 97.37 mmol) was added a little at a time to a solution of 2-(3-hydroxypropyl)-benzimidazole (15.60 g, 88.52 mmol) in DMF (265 ml) and triethylamine (20.27 ml, 145.41 mmol). The mixture was stirred at RT overnight and then admixed with water (800 ml) and extracted with diethyl ether. The organic phase was dried over sodium sulphate and chromatographed over silica gel (mobile phase: cyclohexane/ethyl acetate=6:1), giving 25 g (97%) of colourless crystals. MS (DCI): 291 (M+H)+

Workup

  1. extractionextracted with diethyl ether
  2. dry with materialThe organic phase was dried over sodium sulphate
  3. customchromatographed over silica gel (mobile phase: cyclohexane/ethyl acetate=6:1)

Sources & evidence

ORD record
ord-fcb477d18a744f849491a493dcf7f30a
Source dataset
uspto-grants-2006_01
Patent number
US06984642B1

Linked notes

Loading…