Imidazole → 1-(Tert-butyldiphenylsilyloxymethyl)-2,6-dimethyl-3-nitrobenzene

HRID 636490Notes

Reaction equation

HRID 636490 reaction equation
[Si:1](Cl)([C:14]([CH3:17])([CH3:16])[CH3:15])([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:19][C:20]1[C:27]([N+:28]([O-:30])=[O:29])=[CH:26][CH:25]=[C:24]([CH3:31])[C:21]=1[CH2:22][OH:23].N1C=CN=C1>CN(C)C=O>[Si:1]([O:23][CH2:22][C:21]1[C:24]([CH3:31])=[CH:25][CH:26]=[C:27]([N+:28]([O-:30])=[O:29])[C:20]=1[CH3:19])([C:14]([CH3:17])([CH3:16])[CH3:15])([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 795ImidazoleHCID 94078tert-ButyldiphenylchlorosilaneHCID 10487641(2,6-Dimethyl-3-nitrophenyl)methanol

Product 1

HCID 107645571-(Tert-butyldiphenylsilyloxymethyl)-2,6-dimethyl-3-nitrobenzeneYield 109.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of tert-butyldiphenylsilyl chloride (30.7 g) in dimethylformamide (90 ml) was added 2,6-dimethyl-3-nitrobenzyl alcohol (18.4 g), and imidazole (8.99 g) was added thereto under ice-cooling. The mixture was stirred for 15 minutes at the same temperature and then for 3 hours at ambient temperature. The reaction mixture was poured into ice water, and extracted with ethyl acetate. The organic layer was washed with water and brine, dried over magnesium sulfate and evaporated in vacuo to give 1-(tert-butyldiphenylsilyloxymethyl)-2,6-dimethyl-3-nitrobenzene (46.67 g) as pale yellow oil.

Workup

  1. additionwas added
  2. temperatureunder ice-cooling
  3. waitfor 3 hours at ambient temperature
  4. extractionextracted with ethyl acetate
  5. washThe organic layer was washed with water and brine
  6. dry with materialdried over magnesium sulfate
  7. customevaporated in vacuo

Sources & evidence

ORD record
ord-16c5a157b4754663bcae658cc76bcc8d
Source dataset
uspto-grants-2001_02
Patent number
US06194396B1

Reaction notes

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