2-Aminophenol → O-tert-butyldimethylsilyl-2-aminophenol

HRID 416256Notes

Reaction equation

HRID 416256 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[OH:8].[Si:9](Cl)([C:12]([CH3:15])([CH3:14])[CH3:13])([CH3:11])[CH3:10].CCN(CC)CC>C(Cl)Cl>[C:12]([Si:9]([CH3:11])([CH3:10])[O:8][C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=1[NH2:1])([CH3:15])([CH3:14])[CH3:13]

Participants

5

Reactant 3

HCID 58012-AminophenolHCID 8471TriethylamineHCID 28928tert-Butyldimethylsilyl chloride

Product 1

HCID 20785772O-tert-butyldimethylsilyl-2-aminophenolYield 91%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of 2-aminophenol (3.00 g, 27.5 mmol) in DCM (150 ml) was added tert-butyldimethylsilyl chloride (4.35 ml, 28.9 mmol) and Et3N (4.02 ml, 28.9 mmol). The reaction mixture was stirred 16 h at room temperature. The organic phase was washed with water and brine, dried over anhydrous MgSO4, filtered and concentrated. The residue was purified by flash chromatography (5% AcOEt in hexane) to afford the title compound 196 (5.56 g, 91% yield). 1H NMR (CDCl3) δ (ppm): 7.61 (s, 1H), 7.16 (s, 1H), 6.58 (s, 2H), 6.45 (s, 1H), 6.09 (s, 1H), 3.97 (s, 3H), 3.93 (s, 3H), 3.84 (s, 3H), 3.83 (s, 6H). m/z: 224.1 (MH+).

Workup

  1. washThe organic phase was washed with water and brine
  2. dry with materialdried over anhydrous MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe residue was purified by flash chromatography (5% AcOEt in hexane)

Sources & evidence

ORD record
ord-6462c946e47146aaa2cc871552ccf052
Source dataset
uspto-grants-2012_01
Patent number
US08088805B2

Reaction notes

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