Imidazole → [1-(3-Chlorophenyl)-2-nitroethoxy]triethylsilane

HRID 2377959Notes

Reaction equation

HRID 2377959 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:8]([OH:13])[CH2:9][N+:10]([O-:12])=[O:11])[CH:5]=[CH:6][CH:7]=1.N1C=CN=C1.Cl[Si:20]([CH2:25][CH3:26])([CH2:23][CH3:24])[CH2:21][CH3:22]>CN(C=O)C>[Cl:1][C:2]1[CH:3]=[C:4]([CH:8]([O:13][Si:20]([CH2:25][CH3:26])([CH2:23][CH3:24])[CH2:21][CH3:22])[CH2:9][N+:10]([O-:12])=[O:11])[CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 795ImidazoleHCID 13819ChlorotriethylsilaneHCID 11413010HCID 11413010, compound

Product 1

HCID 22021350[1-(3-Chlorophenyl)-2-nitroethoxy]triethylsilaneYield 91%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of l-(3-chloro-phenyl)-2-nitro-ethanol (26 g, 0.14 mol) in DMF (50 mL) were added imidazole (28.6 g, 0.42 mol) and chlorotriethylsilane (25.3 g, 0.17 mol). The reaction mixture was stirred at room temperature for 2 h. After quenching with water, the mixture was extracted with ethyl acetate. The combined organic layers were washed with water and brine, dried over Na2SO4, and filtered. After removal of solvent, the crude product was purified by flash chromatography (2% EtOAc/hexane) to yield the title compound (37 g, 91%) as a colorless oil. 1H NMR (300 MHz, CDCl3) δ 7.40 (1H, s), 7.27-7.32 (3H, m), 5.40 (1H, dd, J=3.2, 9.5 Hz), 4.51 (1H, dd, J=9.5, 12.1 Hz), 4.36 (1H, dd, J=3.3, 12.1 Hz), 0.85 (9H, t, J=7.5 Hz), 0.54 (6H, q, J=7.5 Hz).

Workup

  1. customAfter quenching with water
  2. extractionthe mixture was extracted with ethyl acetate
  3. washThe combined organic layers were washed with water and brine
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. customAfter removal of solvent
  7. customthe crude product was purified by flash chromatography (2% EtOAc/hexane)

Sources & evidence

ORD record
ord-fa3e0162521c441cb911ad3702f72333
Source dataset
uspto-grants-2008_12
Patent number
US07470713B2

Reaction notes

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