Imidazole → 4-[2-(Tert-butyldiphenylsilyloxy)ethyl]nitrobenzene

HRID 1858303Notes

Reaction equation

HRID 1858303 reaction equation
[N+:1]([C:4]1[CH:12]=[CH:11][C:7]([CH2:8][CH2:9][OH:10])=[CH:6][CH:5]=1)([O-:3])=[O:2].[C:13]([Si:17](Cl)([C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)([CH3:16])([CH3:15])[CH3:14].N1C=CN=C1>CN(C)C=O>[Si:17]([O:10][CH2:9][CH2:8][C:7]1[CH:6]=[CH:5][C:4]([N+:1]([O-:3])=[O:2])=[CH:12][CH:11]=1)([C:13]([CH3:16])([CH3:15])[CH3:14])([C:24]1[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=1)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

Participants

5

Reactant 3

HCID 795ImidazoleHCID 74944-Nitrophenethyl alcoholHCID 94078tert-Butyldiphenylchlorosilane

Product 1

HCID 221251124-[2-(Tert-butyldiphenylsilyloxy)ethyl]nitrobenzeneYield 89.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution containing 3 g (18 mmol) of 4-nitrophenethyl alcohol, 5.2 ml (20 mmol) of tert-butylchlorodiphenylsilane, 3.05 g (45 mmol) of imidazole and 438 mg (3.5 mmol) of N,N-dimethylaminopyridine in dimethylformamide (20 ml) was stirred under a nitrogen atmosphere at room temperature for 3 hours. The solvent was evaporated and the residue partitioned between ethyl acetate (40 ml) and 2M hydrochloric acid (40 ml). The ethyl acetate layer was separated, washed with saturated aqueous sodium bicarbonate (40 ml), dried over magnesium sulfate, filtered and evaporated to give 6.56 g of 4-[2-(tert-butyldiphenylsilyloxy) ethyl]nitrobenzene as a yellow gum.

Workup

  1. customThe solvent was evaporated
  2. customthe residue partitioned between ethyl acetate (40 ml) and 2M hydrochloric acid (40 ml)
  3. customThe ethyl acetate layer was separated
  4. washwashed with saturated aqueous sodium bicarbonate (40 ml)
  5. dry with materialdried over magnesium sulfate
  6. filtrationfiltered
  7. customevaporated

Sources & evidence

ORD record
ord-623aadb3748b4885a27e5c4c5a8cd71a
Source dataset
uspto-grants-2000_11
Patent number
US06150373

Reaction notes

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