Imidazole → HCID 15453718, compound

HRID 601499Notes

Reaction equation

HRID 601499 reaction equation
[Si:1](Cl)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].[N+:9]([C:12]1[CH:13]=[C:14]([OH:20])[C:15]([O:18]C)=[CH:16][CH:17]=1)([O-:11])=[O:10].N1C=CN=[CH:22]1>CN(C=O)C>[C:4]([Si:1]([O:18][C:15]1[CH:16]=[CH:17][C:12]([N+:9]([O-:11])=[O:10])=[CH:13][C:14]=1[O:20][CH3:22])([CH3:3])[CH3:2])([CH3:7])([CH3:6])[CH3:5]

Participants

5

Reactant 3

HCID 795ImidazoleHCID 28928tert-Butyldimethylsilyl chlorideHCID 694712-Methoxy-5-nitrophenol

Product 1

HCID 15453718HCID 15453718, compoundYield 95%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Add tert-butyl-dimethylsilylchloride (14 g, 90 mmol) to a solution of 4-nitroguaiacol (5 g, 30 mmol) in DMF (250 mL) and then add imidazole (6.13 g, 90 mmol). Stir the mixture at room temperature for 16 h. Quench the reaction mixture with water (150 mL). Extract with diethyl ether (3×200 mL). Wash the combined organic portions with water, brine, and dry over MgSO4. Filter and concentrate to a residue. Purify the residue by silica gel flash chromatography, eluting with 15% ethylacetate:hexanes to give the title compound (8.053 g, 95%) as a pale yellow oil. MS (ES+) 284.1 (M+1)+. 1H NMR (CDCl3): δ 7.79 (dd, J=7.8 Hz, 2.7 Hz, 1H), 7.26 (d, J=2.7 Hz, 1H), 6.69 (d, J=7.8 Hz 1H), 3.85 (s, 3H), 0.96 (s, 9H), 0.18 (s, 6H).

Workup

  1. customQuench the reaction mixture with water (150 mL)
  2. extractionExtract with diethyl ether (3×200 mL)
  3. washWash the combined organic portions with water, brine
  4. dry with materialdry over MgSO4
  5. filtrationFilter
  6. concentrationconcentrate to a residue
  7. customPurify the residue by silica gel flash chromatography
  8. washeluting with 15% ethylacetate

Sources & evidence

ORD record
ord-6870eefd147b48de9ab4c0e31f989186
Source dataset
uspto-grants-2011_03
Patent number
US07902356B2

Reaction notes

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