Imidazole → 1-t-Butyldimethylsilyloxyethylbenzimidazole

HRID 2231236Notes

Reaction equation

HRID 2231236 reaction equation
O1CCCC1.[OH:6][CH:7]([C:9]1[NH:10][C:11]2[CH:17]=[CH:16][CH:15]=[CH:14][C:12]=2[N:13]=1)[CH3:8].[Si:18](Cl)([C:21]([CH3:24])([CH3:23])[CH3:22])([CH3:20])[CH3:19].N1C=CN=C1>O>[Si:18]([O:6][CH:7]([C:9]1[NH:13][C:12]2[CH:14]=[CH:15][CH:16]=[CH:17][C:11]=2[N:10]=1)[CH3:8])([C:21]([CH3:24])([CH3:23])[CH3:22])([CH3:20])[CH3:19]

Participants

6

Reactant 4

HCID 795ImidazoleHCID 8028TetrahydrofuranHCID 28928tert-Butyldimethylsilyl chlorideHCID 2059221-(1H-1,3-benzodiazol-2-yl)ethan-1-ol

Product 1

HCID 780646951-t-Butyldimethylsilyloxyethylbenzimidazole

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A solution of 50 ml of tetrahydrofuran containing 2.5 g (15.4 mmoles) of 1-hydroxyethylbenzimidazole, 2.3 g (15.4 mmoles) of t-butyldimethylsilyl chloride and 1.0 g (15.4 mmoles) of imidazole was allowed to stir overnight at room temperature. The reaction mixture was poured into water and the product extracted with ethyl acetate (2×100 ml). The combined extracts were dried over magnesium sulfate and concentrated in vacuo to a colorless oil, 3.5 g. The intermediate was purified by chromatography on 100 g of silica gel using chloroform as the eluent, 3.11 g.

Workup

  1. extractionthe product extracted with ethyl acetate (2×100 ml)
  2. dry with materialThe combined extracts were dried over magnesium sulfate
  3. concentrationconcentrated in vacuo to a colorless oil, 3.5 g
  4. customThe intermediate was purified by chromatography on 100 g of silica gel

Sources & evidence

ORD record
ord-b0c83c28cbe84285a3a170a500fc5bdc
Source dataset
uspto-grants-1988_11
Patent number
US04782050

Reaction notes

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