Imidazole → HCID 22671917, compound

HRID 1003954Notes

Reaction equation

HRID 1003954 reaction equation
[Cl:1][CH2:2][CH2:3][CH2:4][CH2:5][OH:6].[Si:7](Cl)([C:10]([CH3:13])([CH3:12])[CH3:11])([CH3:9])[CH3:8].N1C=CN=C1.CN(C)C=[O:23]>CCCCCC>[Si:7]([O:6][CH:5]([OH:23])[CH2:4][CH2:3][CH2:2][Cl:1])([C:10]([CH3:13])([CH3:12])[CH3:11])([CH3:9])[CH3:8]

Participants

6

Reactant 4

HCID 795ImidazoleHCID 6228DimethylformamideHCID 135694-Chloro-1-butanolHCID 28928tert-Butyldimethylsilyl chloride

Product 1

HCID 22671917HCID 22671917, compoundYield 56%

Reagents, catalysts & solvents 1

HCID 8058HexaneSolvent

Procedure

4-Chloro-1-butanol (5.43 g, 50 mmol) was dissolved in dimethylformamide (50 mL) and tert-butyldimethylsilylchloride (7.54 g, 50 mmol) was added, followed by imidazole (3.4 g, 50 mmol). After 24 hours of stirring at room temperature, the reaction mixture was diluted with hexane, washed with water and brine and dried over anhydrous sodium sulfate. The solvent was evaporated to give colorless liquid which was purified by chromatography on silica gel eluting with hexane/ethyl acetate (30:1) to give the product (7.26 g, 56%). 1H NMR (CDCl3) δ: 0.05 (s, 6H), 0.89 (s, 9 H), 1.64-1.68 (m, 2H), 1.82-1.86 (m, 2H), 3.57 (t, 2H), 3.64 (t, 2 H).

Workup

  1. washwashed with water and brine
  2. dry with materialdried over anhydrous sodium sulfate
  3. customThe solvent was evaporated
  4. customto give colorless liquid which
  5. customwas purified by chromatography on silica gel eluting with hexane/ethyl acetate (30:1)

Sources & evidence

ORD record
ord-ad2c9c9f87a14a709882f39006c4b5f2
Source dataset
uspto-grants-2000_04
Patent number
US06048858

Reaction notes

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