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

HRID 852936Notes

Reaction equation

HRID 852936 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-4d8cea61b0a847d297bc519e085a6c1e
Source dataset
uspto-grants-2007_08
Patent number
US07253204B2

Reaction notes

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