Catechol → Phenol, 2-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-

HRID 1080899Notes

Reaction equation

HRID 1080899 reaction equation
[C:1]1([C:3](=[CH:5][CH:6]=[CH:7][CH:8]=1)[OH:4])[OH:2].N1C=CN=C1.[Si:14](Cl)([C:17]([CH3:20])([CH3:19])[CH3:18])([CH3:16])[CH3:15]>CN(C)C=O>[Si:14]([O:2][C:1]1[CH:8]=[CH:7][CH:6]=[CH:5][C:3]=1[OH:4])([C:17]([CH3:20])([CH3:19])[CH3:18])([CH3:16])[CH3:15]

Participants

5

Reactant 3

HCID 289CatecholHCID 795ImidazoleHCID 28928tert-Butyldimethylsilyl chloride

Product 1

HCID 10878826Phenol, 2-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-Yield 66%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a stirred solution of catechol (5.5 g; 50 mmol) in 20 mL of dimethylformamide was added imidazole (7.14 g; 105 mmol) and t-butyldimethylsilylchloride (7.53 g; 50 mmol). The reaction mixture was stirred for 3 hours after which time TLC showed the reaction to be complete. The reaction mixture was chromatographed directly onto silica gel and eluted with 5% ethyl acetate in hexane to give 7.4 g (66%) of the monosilyl catechol 16. NMR (CDCl3) δ6.963 (dd, J=8.0, 1.6 Hz, 1H, ArH), 6.891 (dt, J=8.0, 2.0 Hz, 1H, ArH), 6.847 (dd, J=8.0, 1.6 Hz, 1H, ArH), 6.773 (dt, J=7.6, 1.6 Hz, 1H, ArH), 5.518 (s, 1H, OH), 0.996 (s, 9H, CCH3), 0.252 (s, 6H, SiCH3); 13C NMR (CDCl3) δ147.250, 142.550, 122.143, 119.989, 117.835, 114.870, 25.730, 18.193, -4.322.

Workup

  1. customthe reaction
  2. customThe reaction mixture was chromatographed directly onto silica gel
  3. washeluted with 5% ethyl acetate in hexane

Sources & evidence

ORD record
ord-7f5534bfff214f16bdfcecc9aa26bd1e
Source dataset
uspto-grants-1996_12
Patent number
US05583235

Reaction notes

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