Imidazole → 5-[[[(1,1-Dimethylethyl)dimethylsilyl]oxy]methyl]-2-methylbenzenamine

HRID 1802468Notes

Reaction equation

HRID 1802468 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([CH2:9][OH:10])[CH:5]=[CH:6][C:7]=1[CH3:8].[C:11]([Si:15]([CH3:18])([CH3:17])Cl)([CH3:14])([CH3:13])[CH3:12].N1C=CN=C1.O>CN(C=O)C.CCOC(C)=O>[Si:15]([O:10][CH2:9][C:4]1[CH:5]=[CH:6][C:7]([CH3:8])=[C:2]([CH:3]=1)[NH2:1])([C:11]([CH3:14])([CH3:13])[CH3:12])([CH3:18])[CH3:17]

Participants

7

Reactant 4

HCID 795ImidazoleHCID 962WaterHCID 28928tert-Butyldimethylsilyl chlorideHCID 586243(3-Amino-4-methylphenyl)methanol

Product 1

HCID 185424035-[[[(1,1-Dimethylethyl)dimethylsilyl]oxy]methyl]-2-methylbenzenamine

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of (3-amino-4-methylphenyl)methanol (1.0 g, 7.3 mmol) in DMF (7.3 mL) was added tert-butyldimethylchlorosilane (1.2 g, 8.1 mmol) and imidazole (0.65 g, 9.5 mmol). The reaction stirred at room temperature for 18 hours and then was poured into a separatory funnel with water and EtOAc. The mixture was extracted with EtOAc and the extracts were washed with brine, dried over MgSO4 and concentrated in vacuo. Purification by silica gel column chromatography (0-40% EtOAc/heptane) afforded the title compound.

Workup

  1. extractionThe mixture was extracted with EtOAc
  2. washthe extracts were washed with brine
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated in vacuo
  5. customPurification by silica gel column chromatography (0-40% EtOAc/heptane)

Sources & evidence

ORD record
ord-f957ee5d8e1f4e4592a08d4bc37141dc
Source dataset
uspto-grants-2013_01
Patent number
US08349865B2

Reaction notes

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