Tert-butyl(2-methoxy-5-nitrophenoxy)dimethylsilane → 3-[(Tert-butyldimethylsilyl)oxy]-4-methoxyaniline

HRID 448341Notes

Reaction equation

HRID 448341 reaction equation
[C:1]([Si:5]([O:8][C:9]1[CH:14]=[C:13]([N+:15]([O-])=O)[CH:12]=[CH:11][C:10]=1[O:18][CH3:19])([CH3:7])[CH3:6])([CH3:4])([CH3:3])[CH3:2].[H][H]>C(OCC)(=O)C.[Pd]>[Si:5]([O:8][C:9]1[CH:14]=[C:13]([NH2:15])[CH:12]=[CH:11][C:10]=1[O:18][CH3:19])([C:1]([CH3:4])([CH3:3])[CH3:2])([CH3:7])[CH3:6]

Participants

5

Reactant 2

HCID 12992941Tert-butyl(2-methoxy-5-nitrophenoxy)dimethylsilaneHCID 178418361HCID 178418361, compound

Product 1

HCID 154537193-[(Tert-butyldimethylsilyl)oxy]-4-methoxyanilineYield 74%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of tert-butyl-(2-methoxy-5-nitrophenoxy)dimethylsilane (3.0 g, 10.6 mmol) and 5% Pd—C (0.3 g) in 30 mL of ethyl acetate was hydrogenated under 50 psi of hydrogen gas for 14 hours. The mixture was filtered through Celite and the filtrate was evaporated. The residue was chromatographed using a hexanes-ethyl acetate gradient, eluting 2.0 g of the product at 85:15 hexanes-ethyl acetate, in 74% yield: 1H NMR (CDCl3) δ 0.15 (s, 6H), 0.99 (s, 9H), 3.37 (br, 2H), 3.72 (s, 3H), 6.23-6.29 (m, 2H), 6.68 (d, J=8.1 Hz, 1H).

Workup

  1. filtrationThe mixture was filtered through Celite
  2. customthe filtrate was evaporated
  3. customThe residue was chromatographed
  4. washeluting 2.0 g of the product at 85:15 hexanes-ethyl acetate

Sources & evidence

ORD record
ord-32fe787fe63648c9b597e36beb16beaa
Source dataset
uspto-grants-2013_07
Patent number
US08481568B2

Reaction notes

Loading…