Water → Tert-butyl(2-methoxy-5-nitrophenoxy)dimethylsilane

HRID 448340Notes

Reaction equation

HRID 448340 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([N+:9]([O-:11])=[O:10])=[CH:5][C:4]=1[OH:12].[Si:13](Cl)([C:16]([CH3:19])([CH3:18])[CH3:17])([CH3:15])[CH3:14].C(N(C(C)C)C(C)C)C.O>CN(C=O)C>[C:16]([Si:13]([O:12][C:4]1[CH:5]=[C:6]([N+:9]([O-:11])=[O:10])[CH:7]=[CH:8][C:3]=1[O:2][CH3:1])([CH3:15])[CH3:14])([CH3:19])([CH3:18])[CH3:17]

Participants

6

Reactant 4

HCID 962WaterHCID 28928tert-Butyldimethylsilyl chlorideHCID 694712-Methoxy-5-nitrophenolHCID 81531Diisopropylethylamine

Product 1

HCID 12992941Tert-butyl(2-methoxy-5-nitrophenoxy)dimethylsilaneYield 64%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 2-methoxy-5-nitrophenol (3.0 g, 17.8 mmol), tert-butyldimethylsilyl chloride (3.2 g, 21.4 mmol), and ethyldiisopropylamine (5.8 g, 44.5 mmol) in DMF (50 mL) was stirred at room temperature for 3 hours. The mixture was poured into water (100 mL) and extracted with methylene chloride (3×100 mL). The combined organic extracts were washed with water (5×100 mL) and dried (MgSO4), and the solvent was evaporated under vacuum. The residue was recrystallized from ethanol-water, providing 3.2 g of the product as white crystals, in 64% yield: 1H NMR (CDCl3) δ 0.19 (s, 6H), 1.01 (s, 9H), 3.91 (s, 3H), 6.89 (d, J=8.9 Hz, 1H), 7.71 (d, J=2.8 Hz, 1H), 7.89 (dd, J=8.9 Hz, J=2.8 Hz, 1H).

Workup

  1. extractionextracted with methylene chloride (3×100 mL)
  2. washThe combined organic extracts were washed with water (5×100 mL)
  3. dry with materialdried (MgSO4)
  4. customthe solvent was evaporated under vacuum
  5. customThe residue was recrystallized from ethanol-water

Sources & evidence

ORD record
ord-d083226a6e384907894da95173c5e4d8
Source dataset
uspto-grants-2013_07
Patent number
US08481568B2

Reaction notes

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