Imidazole → HCID 19432375, compound

HRID 1736294Notes

Reaction equation

HRID 1736294 reaction equation
[N+:1]([CH:4]([CH3:8])[CH:5]([OH:7])[CH3:6])([O-:3])=[O:2].N1C=CN=C1.[Si:14](Cl)([C:17]([CH3:20])([CH3:19])[CH3:18])([CH3:16])[CH3:15]>CN(C)C=O>[N+:1]([CH:4]([CH3:8])[CH:5]([O:7][Si:14]([C:17]([CH3:20])([CH3:19])[CH3:18])([CH3:16])[CH3:15])[CH3:6])([O-:3])=[O:2]

Participants

5

Reactant 3

HCID 795ImidazoleHCID 28928tert-Butyldimethylsilyl chlorideHCID 930253-Nitrobutan-2-ol

Product 1

HCID 19432375HCID 19432375, compoundYield 101.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

2.4 g (20 mmol) of 3-nitro-2-butanol was dissolved in 10 ml of dimethylformamide, 4.08 g (60 mmol) of imidazole and 4.52 g (30 mmol) of tert-butyldimethylsilyl chloride were added under ice cooling, and the mixture was stirred at room temperature for 6 hours. After the reaction, the reaction solution was poured into 100 ml of ice water, and the mixture was extracted with diethyl ether. The organic layer was washed successively with 2N hydrochloric acid, saturated sodium bicarbonate solution and saturated saline, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The residue was purified with silica gel column chromatography (hexane-benzene=10:1) to give 4.73 g of 3-nitro-2-(tert-butyldimethylsilyloxy)butane as a colorless oil (yield: quantitative).

Workup

  1. customAfter the reaction
  2. extractionthe mixture was extracted with diethyl ether
  3. washThe organic layer was washed successively with 2N hydrochloric acid, saturated sodium bicarbonate solution and saturated saline
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified with silica gel column chromatography (hexane-benzene=10:1)

Sources & evidence

ORD record
ord-9b7580035c83480fbab840358f9b9dfa
Source dataset
uspto-grants-1996_07
Patent number
US05541169

Reaction notes

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