Imidazole → HCID 58994475, compound

HRID 1190215Notes

Reaction equation

HRID 1190215 reaction equation
[CH3:1][C:2]([C:6]1[CH:11]=[CH:10][C:9]([N+:12]([O-:14])=[O:13])=[CH:8][CH:7]=1)([CH3:5])[CH2:3][OH:4].[Si:15](Cl)([C:18]([CH3:21])([CH3:20])[CH3:19])([CH3:17])[CH3:16].N1C=CN=C1>C(Cl)Cl>[C:18]([Si:15]([CH3:17])([CH3:16])[O:4][CH2:3][C:2]([CH3:1])([C:6]1[CH:11]=[CH:10][C:9]([N+:12]([O-:14])=[O:13])=[CH:8][CH:7]=1)[CH3:5])([CH3:21])([CH3:20])[CH3:19]

Participants

5

Reactant 3

HCID 795ImidazoleHCID 28928tert-Butyldimethylsilyl chlorideHCID 222492792-Methyl-2-(4-nitrophenyl)propan-1-ol

Product 1

HCID 58994475HCID 58994475, compoundYield 65%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a mixture of 2-methyl-2-(4-nitro-phenyl)-propan-1-ol (as prepared in the previous step, 1.50 g, 7.68 mmol) and t-butyl-dimethylsilyl chloride (1.51 g, 9.99 mmol) in 60 mL of DCM was slowly added imidazole (3.09 g, 45.4 mmol). After stirring at RT for 16 h, the mixture was treated with 40 mL of DCM and washed with H2O (30 mL), 15% aqueous citric acid (30 mL) and brine (20 mL). The organic layer was dried (Na2SO4) and concentrated in vacuo. The residue was purified by flash chromatography on silica gel (0-5% EtOAc/hexane) to give 1.82 g (65%) of the title compound as a light brown oil. 1H-NMR (CDCl3; 400 MHz): δ 7.85 (d, 2H, J=8.8 Hz), 7.52 (d, 2H, J=8.8 Hz), 3.59 (s, 2H), 1.35 (s, 6H), 0.86 (s, 9H), −0.04 (s, 6H).

Workup

  1. washwashed with H2O (30 mL), 15% aqueous citric acid (30 mL) and brine (20 mL)
  2. dry with materialThe organic layer was dried (Na2SO4)
  3. concentrationconcentrated in vacuo
  4. customThe residue was purified by flash chromatography on silica gel (0-5% EtOAc/hexane)

Sources & evidence

ORD record
ord-87c08e3df14945e8bfc5f74dee5a94d4
Source dataset
uspto-grants-2014_03
Patent number
US08674100B2

Reaction notes

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