Imidazole → 3-({[Tert-butyl(dimethyl)silyl]oxy}methyl)-5-methylaniline

HRID 968242Notes

Reaction equation

HRID 968242 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([CH2:9][OH:10])[CH:5]=[C:6]([CH3:8])[CH:7]=1.N1C=CN=C1.[CH3:16][C:17]([Si:20](Cl)([CH3:22])[CH3:21])([CH3:19])[CH3:18]>C(Cl)Cl.O>[Si:20]([O:10][CH2:9][C:4]1[CH:3]=[C:2]([CH:7]=[C:6]([CH3:8])[CH:5]=1)[NH2:1])([C:17]([CH3:19])([CH3:18])[CH3:16])([CH3:22])[CH3:21]

Participants

6

Reactant 3

HCID 795ImidazoleHCID 28928tert-Butyldimethylsilyl chlorideHCID 15680639(3-Amino-5-methylphenyl)methanol

Product 1

HCID 697356593-({[Tert-butyl(dimethyl)silyl]oxy}methyl)-5-methylaniline

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of (3-amino-5-methylphenyl)methanol (prepared according to: Behrens, C.; Egholm, M.; Buchardt, O. Synthesis 1992, 12, 1235-1236, 750 mg, 5.47 mmol) in CH2Cl2 (25 mL) was added imidazole (447 mg, 6.56 mmol) then TBDMSCl (989 mg, 6.56 mmol) at room temperature. After 72 hours the mixture was diluted with H2O. The layers were separated and the aqueous extracted with CH2Cl2 (2×). The combined organic layers were dried (MgSO4), filtered, and concentrated. Flash column chromatography (20% EtOAc/hexanes) gave 3-({[tert-butyl(dimethyl)silyl]oxy}methyl)-5-methylaniline as a clear oil. 1H-NMR (300 MHz, CDCl3) δ 6.58 (s, 1H), 6.50 (s, 1H), 6.40 (s, 1H), 4.60 (s, 2H), 3.60 (bs, 2H), 2.24 (s, 3H).

Workup

  1. customat room temperature
  2. customThe layers were separated
  3. extractionthe aqueous extracted with CH2Cl2 (2×)
  4. dry with materialThe combined organic layers were dried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-b95139b03b1440588619ef554c406d24
Source dataset
uspto-grants-2005_10
Patent number
US06958340B2

Reaction notes

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