Imidazole → 2-(3-Tert-butyldimethylsilyloxyprop-2-enyl)nitrobenzene

HRID 1106935Notes

Reaction equation

HRID 1106935 reaction equation
[C:1]([Si:5]([CH3:8])([CH3:7])Cl)([CH3:4])([CH3:3])[CH3:2].[N+:9]([C:12]1[CH:21]=[CH:20][CH:19]=[CH:18][C:13]=1[CH:14]=[CH:15][CH2:16][OH:17])([O-:11])=[O:10].N1C=CN=C1>CN(C=O)C>[Si:5]([O:17][CH:16]=[CH:15][CH2:14][C:13]1[CH:18]=[CH:19][CH:20]=[CH:21][C:12]=1[N+:9]([O-:11])=[O:10])([C:1]([CH3:4])([CH3:3])[CH3:2])([CH3:8])[CH3:7]

Participants

5

Reactant 3

HCID 795ImidazoleHCID 28928tert-Butyldimethylsilyl chlorideHCID 533957172-Nitrocinnamyl alcohol

Product 1

HCID 544712302-(3-Tert-butyldimethylsilyloxyprop-2-enyl)nitrobenzene

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Tert-butyldimethylchlorosilane (5.10 g, 33.8 mmol) was added to a solution of 2-nitrocinnamyl alcohol (5.05 g, 28.2 mmol) and imidazole (2.88 g, 42.3 mmol) in DMF (100 ml). After stirring at room temperature for 18 hours the reaction mixture was partitioned between water (200 ml) and ethyl acetate (200 ml). The organic layer was separated washed with brine (2×m 100 ml) and dried (MgSO4). Filtration and evaporation of the solvent gave the crude product which was purified by flash chromatography on silica gel with ethyl acetate-hexane (1:3) as eluant. (7.82 g, 95%).

Workup

  1. customwas partitioned between water (200 ml) and ethyl acetate (200 ml)
  2. customThe organic layer was separated
  3. washwashed with brine (2×m 100 ml)
  4. dry with materialdried (MgSO4)
  5. filtrationFiltration and evaporation of the solvent

Sources & evidence

ORD record
ord-0c430a21c3624f98b5b22922ad7c68ea
Source dataset
uspto-grants-2000_05
Patent number
US06057311

Reaction notes

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