Imidazole → (3-Benzyloxy-4-nitrophenoxy)-tert-butyldimethylsilane

HRID 660509Notes

Reaction equation

HRID 660509 reaction equation
[CH2:1]([O:8][C:9]1[CH:10]=[C:11]([OH:18])[CH:12]=[CH:13][C:14]=1[N+:15]([O-:17])=[O:16])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:19]([Si:23]([CH3:26])([CH3:25])Cl)([CH3:22])([CH3:21])[CH3:20].N1C=CN=C1.CN(C1C=CC=CN=1)C>CN(C=O)C.CCOC(C)=O>[CH2:1]([O:8][C:9]1[CH:10]=[C:11]([CH:12]=[CH:13][C:14]=1[N+:15]([O-:17])=[O:16])[O:18][Si:23]([C:19]([CH3:22])([CH3:21])[CH3:20])([CH3:26])[CH3:25])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

7

Reactant 4

HCID 795ImidazoleHCID 218852-DimethylaminopyridineHCID 28928tert-Butyldimethylsilyl chlorideHCID 109777113-(Benzyloxy)-4-nitrophenol

Product 1

HCID 68839042(3-Benzyloxy-4-nitrophenoxy)-tert-butyldimethylsilane

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 3-benzyloxy-4-nitrophenol (EP application 095121) (6.3 g, 25.7 mmol), t-butyldimethychlorosilane (5.81 g, 38.6 mmol), imidazole (3.5 g, 51.4 mmol), and dimethylaminopyridine (2-3 mg) in DMF (20 mL) is stirred 18 h. The solution is poured into EtOAc and extracted once with water and five times with brine. The organic phase is dried, filtered, and concentrated to afford the title compound: 1H NMR (CDCl3δ 7.73 (d, J=9.1 Hz, 1H), 7.21 (m, 5H), 6.31 (d, J=2.5 Hz, 1H), 6.26 (dd, J=8.8, 2.5 Hz, 1H), 5.02 (s, 2H), 0.78 (s, 9H), 0.00 (s, 6H).

Workup

  1. extractionextracted once with water and five times with brine
  2. customThe organic phase is dried
  3. filtrationfiltered
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-251827faf3e94879b3e26030185221af
Source dataset
uspto-grants-2011_12
Patent number
US08084448B2

Reaction notes

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