Imidazole → 3-(Tert-butyldimethylsilyloxymethyl)aniline

HRID 2235520Notes

Reaction equation

HRID 2235520 reaction equation
[OH:1][CH2:2][C:3]1[CH:4]=[C:5]([CH:7]=[CH:8][CH:9]=1)[NH2:6].N1C=CN=C1.[Si:15](Cl)([C:18]([CH3:21])([CH3:20])[CH3:19])([CH3:17])[CH3:16].O>CN(C=O)C>[Si:15]([O:1][CH2:2][C:3]1[CH:4]=[C:5]([CH:7]=[CH:8][CH:9]=1)[NH2:6])([C:18]([CH3:21])([CH3:20])[CH3:19])([CH3:17])[CH3:16]

Participants

6

Reactant 4

HCID 795ImidazoleHCID 962WaterHCID 28928tert-Butyldimethylsilyl chlorideHCID 802933-Aminobenzyl alcohol

Product 1

HCID 105859773-(Tert-butyldimethylsilyloxymethyl)anilineYield 62.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To 1.00 g (8.1 mmol) of 3-hydroxymethylaniline in 25 mL of DMF was added 0.61 g (8.9 mmol) of imidazole and 1.35 g (8.9 mmol) of tert-butyldimethylsilyl chloride. The reaction was stirred at room temperature for 18 h and poured into 12 volumes of water. The product was extracted with ether and the combined organic layers were washed successively with water and brine, dried over sodium sulfate, filtered and concentrated to a golden oil. The oil was purified by flash chromatography eluting with a 20% ethyl acetate/hexanes mixture to give 1.2 g (62%) of the title compound as a colorless oil.

Workup

  1. extractionThe product was extracted with ether
  2. washthe combined organic layers were washed successively with water and brine
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated to a golden oil
  6. customThe oil was purified by flash chromatography
  7. washeluting with a 20% ethyl acetate/hexanes mixture

Sources & evidence

ORD record
ord-d60200cf16e44e9dba486b1f40d236c8
Source dataset
uspto-grants-2010_05
Patent number
US07714009B2

Reaction notes

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