2-Methyl-4-nitrophenol → HCID 66589491, compound

HRID 588033Notes

Reaction equation

HRID 588033 reaction equation
[CH3:1][C:2]1[CH:7]=[C:6]([N+:8]([O-:10])=[O:9])[CH:5]=[CH:4][C:3]=1[OH:11].[Si:12](Cl)([C:15]([CH3:18])([CH3:17])[CH3:16])([CH3:14])[CH3:13]>CN(C=O)C>[C:15]([Si:12]([CH3:14])([CH3:13])[O:11][C:3]1[CH:4]=[CH:5][C:6]([N+:8]([O-:10])=[O:9])=[CH:7][C:2]=1[CH3:1])([CH3:18])([CH3:17])[CH3:16]

Participants

4

Reactant 2

HCID 74422-Methyl-4-nitrophenolHCID 28928tert-Butyldimethylsilyl chloride

Product 1

HCID 66589491HCID 66589491, compoundYield 75%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 2-methyl-4-nitrophenol (3.0 g, 19.6 mmol), TBS-Cl (3.0 g, 19.6 mmol), and TEA (2.2 g, 21.6 mmol) in DMF (30 mL) stirred at ambient temperature for 16 h. The mixture was partitioned between 10% aqueous sodium bicarbonate solution (100 mL) and ethyl acetate (100 mL), and the aqueous layer was extracted with ethyl acetate (100 mL). The combined organic layers were washed with 10% aqueous sodium bicarbonate (3×100 mL) and water (100 mL), and evaporated under vacuum. The residue was chromatographed in hexanes-ethyl acetate gradient, providing 3.9 g of tert-butyldimethyl(2-methyl-4-nitrophenoxy)silane, in 75% yield; 1H NMR (DMSO-d6) δ 0.29 (s, 6H), 1.00 (s, 9H), 2.24 (s, 3H), 7.03 (d, J=8.9 Hz, 1H), 8.02 (dd, J=2.8, 8.9 Hz, 1H), 8.12 (d, J=2.5 Hz, 1H).

Workup

  1. customThe mixture was partitioned between 10% aqueous sodium bicarbonate solution (100 mL) and ethyl acetate (100 mL)
  2. extractionthe aqueous layer was extracted with ethyl acetate (100 mL)
  3. washThe combined organic layers were washed with 10% aqueous sodium bicarbonate (3×100 mL) and water (100 mL)
  4. customevaporated under vacuum
  5. customThe residue was chromatographed in hexanes-ethyl acetate gradient

Sources & evidence

ORD record
ord-2b4da40cdaeb4b69b6da3c1df463db85
Source dataset
uspto-grants-2016_01
Patent number
US09227954B2

Reaction notes

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